Large NIL Deal, Zero Real Estate Experience — Where Do We Start?

[Jack Andrews]

Hey everyone — my best friend is a college athlete who just received a significant NIL deal. I’m helping him build a real estate strategy around it and we’re both completely new to this. Looking for honest advice from people who’ve actually done it. background: • We have real capital to deploy, looking to start with 1-2 properties and scale • Tax strategy is a priority — depreciation, cost segregation, STR loopholes • I’m considering getting my real estate license to rep him on purchases and manage properties • We want cash flow now and equity long term Questions: 1. For someone prioritizing both cash flow AND tax benefits, is STR always the move or does it depend on the market? When does mid-term or long term actually make more sense? 2. What does a realistic remote STR operation look like — what software, what local team, and how many hours per week once it’s actually running smoothly? 3. We want to start in one market to learn, then expand to a higher yield vacation market. What should we look for when evaluating a first market vs a second more aggressive market? 4. If I get my real estate license purely to rep him and manage his properties — what’s the best brokerage structure for that? I don’t want to be a traditional agent, just want to handle his deals. 5. How early does a sports CPA need to be involved and what should we have in place before the first purchase? Appreciate any real world experience