1. Structure the Security Deposit the Right Way

One of the most overlooked details in any lease is where the security deposit is actually held. I always recommend requesting that your deposit be placed in a neutral escrow account, ideally with a real estate broker or title company rather than a personal account controlled by the landlord. This creates transparency, protects both sides, and establishes a professional standard from the beginning.

It also removes unnecessary tension at move-out, when timelines are tight and expectations need to be clear. In pro sports it is damn near impossible to hand deliver a security check after the lease ends, so having that security deposit with an escrow holder cuts down on the runaround afterward.

2. Document the Property Like a Crime Scene: Before and After Move Out

The moment you gain access to the property, treat it like a closing walkthrough. Take detailed, time-stamped photos and videos of everything. Every room, every surface, every fixture. Open drawers. Open cabinets. Capture the inside of appliances. Document floors, walls, and any existing wear. Then share that documentation with your real estate agent and the landlord immediately. Simply demonstrating to the landlord that you are on the ball will often cut down on squirreliness after the lease ends. I have seen this one step save clients from unnecessary disputes time and time again. It creates a clear record of the home’s condition on day one and keeps everyone aligned when it is time to move out, and how you left the property post move-out.

BONUS: Schedule a professional cleaner to come clean the home after you move out. Even if you are a clean and tidy person and leave the home in great shape, there is something about the landlord walking into a home that has been professionally cleaned that will almost always cut down on security deposit squirreliness.

3. Set Up a Centralized Communication Hub

One of the biggest mistakes I see is communication scattered across too many people and platforms. Your household should operate with the same level of organization as your professional life. I recommend setting up a dedicated email address and phone number specifically for housing and household logistics. Your agent, family office, assistant, and vendors should all be looped into this system. Utilities, maintenance, deliveries, and service coordination can all run through one centralized hub. It keeps everything organized and allows your team to step in seamlessly when needed.

4. Clarify Furnishings and Inventory Upfront

“Furnished” can mean very different things depending on the property. Before you sign, confirm exactly what is included - from furniture to kitchenware, linens, electronics, and outdoor items. If something is essential to your day-to-day life, make sure it is clearly outlined in writing. This is where photos come into play - I also recommend clarifying how damages, replacements, and missing items will be handled during your stay. These details matter more than most people expect.

5. Define Privacy and Access Expectations Early

Privacy is not a luxury when you’re in pro-sports. It is a safety concern and an absolute vital part of the process when you’re negotiating your lease. Before signing, confirm who has access to the property, under what circumstances, and how notice will be given. If there is a property manager involved, establish clear communication protocols and boundaries from the start. Your home during the season should function as a true private space, and that only happens when expectations are clearly defined in advance.