I served as the buyer's agent and property manager for my clients under Blue Chariot Realty & Management.

We will certainly manage the drawdown from those funds to account for tax consequences as best we can.I appreciate the calls for diversification and I get that cash flow is a tougher to secure with interest rates where they are.

Speak with the director of development (they're not always titled that way, so just ask for whoever deals with area developments, new construction, rezoning, etc.) to ask if they'd be supportive of your plan.

It's our least developed beach.

This seems like a no-brainer to me and fits well into a vertical integration strategy (I'm also thinking about managing other people's rentals as even more vertical integration (aka side money).  

Next question.... will you self-manage it, or turn it over to a professional management company, or some type of hybrid? 

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

I invest, flip, and own a property management company in CT. 

However, the tax treatment differs between short-term and long-term rentals:Short-Term Rentals (STRs): If you materially participate (work 100+ hours and more than anyone else on the property), you may be able to offset rental deductions against W-2 or other active income, offering greater tax benefits.Long-Term Rentals (LTRs): If your AGI exceeds $100K, your rental losses may be limited, unless you qualify as a Real Estate Professional (REPS).If you plan to expand your rental portfolio, consider an LLC later for liability protection and easier management.

@Michael Baum how many Short-term rentals do you manage this way where you are on call all the time?