You know what’s funny? Most people think managing one household is complicated. Try coordinating staff across a penthouse in Manhattan, a compound in the Hamptons, and a winter home in Palm Beach. Now you’re playing three-dimensional chess with schedules, travel logistics, and compensation packages that would make your accountant weep.
We’ve been placing estate staff for families with multiple properties for over two decades, and honestly, it never gets simpler. But it does get more interesting. The families who nail this arrangement understand something crucial: you’re not just hiring someone to manage houses. You’re hiring someone to manage the constant motion between them.
Let’s talk about what actually happens when your estate staff works across multiple homes, because the fantasy version and the reality are pretty far apart.
The Geography Problem Nobody Mentions
Nashville to Miami is 875 miles. Your estate manager can’t just pop over to handle a contractor issue at the beach house while simultaneously overseeing a dinner party at the primary residence. Sounds obvious, right? You’d be shocked how many families assume their house manager can somehow be in two places at once.
The first conversation we have with families who own multiple properties usually starts with “So, how often do you actually occupy each home?” Because that answer determines everything. If you’re spending six months in Nashville and six months in Miami, you’re looking at one staffing model. If you’re bouncing between properties every few weeks, you need something completely different.
Some families think they can hire one estate manager who travels with them. That works beautifully until you realize someone needs to be at the empty properties handling maintenance, contractors, deliveries, and the hundred other things that don’t stop just because you’re not there. We’ve watched families try the “we’ll just lock it up when we leave” approach. It usually lasts about six months before something expensive breaks.
The best arrangements we’ve seen involve either a primary estate manager who travels with the family plus property-specific house managers at each location, or a lead estate manager who oversees local teams at each property. Neither option is cheap, but both are cheaper than the alternative, which is properties falling apart when you’re not looking.
What “Traveling with the Family” Actually Means
Let’s get specific about compensation because this is where things get weird fast. Your estate manager isn’t traveling for fun. They’re traveling for work. That means you’re paying for their time in transit, their accommodations if they’re not staying at your property, their meals, and often a premium for the disruption to their personal life.
One family we worked with in Nashville had properties in three cities. They wanted their estate manager to rotate between locations on a monthly basis. Great plan, except they hadn’t thought about the fact that this person would need to maintain a primary residence somewhere, which meant either paying for housing they barely used or expecting them to live out of a suitcase permanently. Neither option attracted the caliber of candidates they wanted.
The families who get this right build travel compensation into the base salary or create a separate travel stipend. They think through the logistics of what happens to the estate manager’s own life when they’re spending 40% of their time on the road. Do they have a family? Pets? A partner with their own career? You’re asking someone to build their entire life around your schedule, and that costs money.
We’ve placed estate managers in multi-property situations where the compensation package included a housing allowance specifically because the travel schedule made maintaining their own home impractical. We’ve seen arrangements where families provide a small apartment or guest house at each property so the estate manager has consistent space wherever they are. And we’ve seen families pay significant premiums for estate managers willing to be essentially nomadic.
The worst arrangements? Families who expect their estate manager to figure out their own accommodations, pay their own travel costs, and accept the same salary they’d earn managing a single property. Those postings sit empty for months.
The Coordination Nightmare
Here’s what a typical week looks like for an estate manager overseeing multiple properties: Monday they’re in Nashville dealing with a plumbing issue. Tuesday they’re on a call with the landscaping crew in Aspen while simultaneously coordinating a furniture delivery in Miami. Wednesday they’re physically in Miami checking on renovation progress. Thursday they’re back in Nashville for a dinner party. Friday they’re trying to remember which property needs the HVAC service and which one needs the pool guy.
Now multiply that across months and years. The organizational skills required are insane.
The estate managers who excel at multi-property coordination use systems that would impress a Fortune 500 operations manager. Shared calendars for each property. Vendor databases organized by location. Separate budgets tracked monthly. Regular check-ins with on-site staff at each location. Video walkthroughs when they can’t be somewhere physically. The technology skills alone are significant.
What doesn’t work is assuming your estate manager will just “keep track of things in their head.” We’ve watched that approach implode spectacularly. Three properties means three completely different vendor relationships, three sets of local regulations, three maintenance schedules, three budgets, and three different sets of family preferences depending on which home you’re in. Nobody’s memory is that good.
The families who run smooth multi-property operations invest in the tools and systems their estate manager needs. Project management software. Expense tracking systems. Communication platforms that keep everyone in the loop. This isn’t optional infrastructure, it’s the baseline requirement for not losing your mind.
Travel Logistics That Sound Simple Until They’re Not
Your estate manager needs to get from Nashville to your ski house in Colorado. Simple, right? Book a flight, done. Except it’s never that simple.
Are you paying for their flight? Obviously, but are you paying for economy or business class? If they’re traveling with household items, do they need to check bags and who’s covering those fees? When they land, are they renting a car or do you have a vehicle at each property? If they’re renting, who’s on the rental agreement and who’s covering the insurance? Are they getting reimbursed for mileage or is it a flat rate?
Now factor in that your estate manager might need to make emergency trips on short notice. The contractor in Miami just found water damage that needs immediate attention. Your estate manager is in Nashville. The flight from Nashville to Miami is $400 today but could be $1,200 tomorrow depending on availability. Do they have authorization to book last-minute travel without approval? What’s the budget ceiling?
We’ve seen families create travel policies for their multi-property estate managers that rival corporate travel departments. Maximum flight costs, preferred booking windows, approved rental car companies, per diem rates for meals when traveling. It sounds excessive until you’re six months in and realize you’ve spent $15,000 on unplanned travel costs because nobody established guidelines.
The estate managers who thrive in these roles appreciate clear policies. They don’t want to be making judgment calls about whether a $600 flight is reasonable or if they should wait two days for a $300 option while your property sits unattended. Give them a framework and let them execute.
The Question of Primary Residence
This is the piece that trips up almost everyone. Where does your multi-property estate manager actually live?
Some families assume their estate manager will maintain their own home and travel as needed. That works if the travel is occasional. It doesn’t work if your estate manager is on the road more than they’re home. Nobody’s paying a mortgage or rent for a place they sleep in twice a month.
Other families assume their estate manager will just live at whichever property the family currently occupies. That sounds reasonable until you think about what happens during the three weeks you’re not anywhere. Your estate manager is bouncing between empty houses with no stable home base and no personal life.
The most successful arrangements we’ve seen establish one property as the estate manager’s primary base. Maybe it’s your main residence. Maybe it’s the property you use least frequently. Either way, it’s where they keep their things, where they return between trips, and where they can actually build some semblance of routine.
Some families provide dedicated living quarters at this primary property. We’ve placed estate managers in situations where they had a guest house at the main estate and hotel accommodations when traveling to other properties. We’ve seen arrangements where the estate manager lived in a separate residence near the primary home and had access to guest rooms at other locations.
What doesn’t work is expecting someone to live out of a suitcase indefinitely while managing complex operations across multiple high-value properties. The burnout rate on that arrangement is measured in months, not years.
Team Structures That Actually Function
Very few families can make a solo estate manager work across multiple properties long-term. The logistics are too complex and the risk is too high. What if they’re in Nashville when something urgent happens in Miami?
The families who get this right build teams. Maybe it’s a lead estate manager who travels with the family plus house managers at each property who report to them. Maybe it’s an estate manager who oversees everything remotely plus property managers at each location. Maybe it’s different specialists for different properties depending on the property’s use and complexity.
We worked with a Nashville family who had four properties. They hired one estate manager as their right hand who traveled with them, plus a house manager at each of the other three properties. The traveling estate manager coordinated everything and handled the family’s direct needs. The house managers kept their assigned properties running and reported to the lead estate manager. It was expensive but it worked flawlessly.
Compare that to families who try to make one person do everything. They end up with an exhausted, overwhelmed estate manager who quits within a year, leaving the family scrambling to replace them while simultaneously learning they should have had a team all along.
Building a team means clear reporting structures. Who’s in charge when the family isn’t present? Who has authority to spend money and how much? Who handles emergencies at each location? The families who document these relationships and communicate them clearly to everyone involved have dramatically fewer problems.
When You’re Never Quite Sure Where Anyone Is
The communication challenges in multi-property staffing are real. Your estate manager is in Miami. You’re in Nashville. You need something handled in Aspen. Do you call the estate manager to coordinate the Aspen house manager? Do you call the Aspen house manager directly? What if there’s a budget question, who approves it?
The families who avoid constant confusion establish clear communication protocols from day one. Maybe there’s a weekly call with all property managers to discuss what’s happening where. Maybe there’s a shared system where everyone logs updates and requests. Maybe there’s a clear chain of command for different types of issues.
What creates chaos is ad hoc communication where the family calls whoever they think of first, different family members give conflicting instructions to different staff, and nobody’s quite sure what’s been handled and what’s still pending. We’ve watched families accidentally tell three different people to handle the same issue because communication wasn’t centralized.
Technology helps but it’s not magic. You still need humans who understand the system and follow it consistently. The best operations we’ve seen combine technology platforms with regular human check-ins. The technology tracks the details, the humans ensure nothing falls through cracks.
The Tax and Legal Complexity
Oh, this is fun. Your estate manager works in three different states. Where do you pay their employment taxes? What about state income tax withholding? If they’re living in Tennessee but spending significant time working in New York and California, what are your obligations?
We’re not accountants, but we’ve seen enough multi-property employment situations to know this gets complicated fast. Many families don’t realize the tax implications until they’re already in the middle of it. You might need separate payroll registrations in each state where your estate manager regularly works. You might need to withhold state taxes based on where work is actually performed, not where the employee lives.
The families who get this right involve employment attorneys and accountants who specialize in household employment from the beginning. They establish where the employee is based, how work across state lines will be handled, and what the tax implications are before anyone starts working.
Trying to figure this out retroactively is expensive and stressful. We’ve known families who ended up owing back taxes and penalties because they didn’t realize they needed to be withholding in multiple states. The estate managers in those situations weren’t thrilled either since they faced unexpected tax bills.
What This Actually Costs
Let’s talk numbers because you need to know what you’re getting into. A top-tier estate manager for a single property in Nashville might earn $100,000 to $150,000 depending on the scope and complexity. An estate manager coordinating multiple properties with travel requirements? You’re looking at $150,000 to $250,000 base, plus benefits, plus travel expenses, plus potentially housing allowances or accommodations.
If you’re building a team with a lead estate manager plus house managers at other properties, multiply that across each position. A house manager at each property might run $75,000 to $125,000 depending on location and responsibilities. So a family with three properties might be looking at $400,000 to $600,000 annually just in estate management payroll before benefits and expenses.
That sounds insane until you calculate what poor property management costs. One major maintenance issue that wasn’t caught early because nobody was consistently monitoring the property can easily run $50,000 to $100,000 in repairs. Vendor fraud or overbilling when there’s no oversight? We’ve seen families lose tens of thousands. Security issues at unoccupied properties?
The families who view multi-property estate management as insurance rather than overhead understand the value proposition. You’re protecting assets worth millions of dollars. You’re ensuring your homes are ready when you want to use them. You’re preventing small problems from becoming catastrophic ones. The cost of doing it right is significant, but the cost of doing it wrong is often higher.
The Burnout Reality
Even estate managers who love their jobs burn out when they’re constantly traveling between properties. The families who retain great staff in multi-property roles recognize this and build in recovery time.
Maybe your estate manager gets extra PTO to compensate for the travel demands. Maybe there are predictable periods when they’re based at one location for several weeks to establish routine. Maybe there’s a rotation where they’re heavily traveling for three months and then more stationary for three months.
What burns people out is unpredictability combined with constant motion. If your estate manager never knows where they’ll be next week and they’re on a plane every three days, they won’t last. The best arrangements balance the family’s legitimate needs with the estate manager’s legitimate need for some stability and personal life.
We’ve placed estate managers who loved the variety of multi-property work. They enjoyed different locations, appreciated the challenge of coordinating complex operations, and thrived on the problem-solving required. But even they needed structure and breaks to sustain that pace long-term.
When It Works and When It Doesn’t
Multi-property estate staffing works beautifully when families have realistic expectations, appropriate budgets, and clear systems. It works when you view it as a complex operation that requires infrastructure and planning, not just hiring someone and hoping they’ll figure it out.
It doesn’t work when families want single-property budgets with multi-property results. It doesn’t work when communication is chaotic and nobody’s clear on who’s responsible for what. It doesn’t work when you expect one person to be everywhere at once.
After twenty years of placing estate staff in these arrangements, we can usually tell within the first conversation whether a family is set up for success or heading for problems. The successful ones ask about systems, communication protocols, team structures, and long-term sustainability. The ones headed for disaster are focused on finding one superhuman who can manage everything for the least amount of money.
If you’re considering multi-property estate staffing, start by honestly assessing how often you use each property, what level of maintenance and oversight each requires, and what you’re willing to invest in getting it right. Then build a structure that matches reality rather than hoping reality will match your wishful thinking.
Your properties are significant investments. Protecting them requires significant resources and planning. But when it’s done right, you have homes that are always ready when you are, properties that hold their value, and peace of mind that someone competent is watching over everything even when you’re not there.
That’s worth investing in properly.
