If you have vacancy or in need of a large repair, will you have the cash to also manage that? 

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.

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

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.

The car/renters/umbrella won't be with Foremost but this way you can have one agent to manage your portfolio.

Trying to get into the nuts and bolts of how he was trying to source a location, project size of preference, what type of financial modeling he does, what kind of tenants he was hoping to attract/the strategy behind it, if he was doing any joint ventures or had done any in the past, if he had taken part in any syndications, what management strategies he was implementing with his current properties to maximize lease uptime and profit, what types of leases he generally favored contracting for his properties--all of that was like pulling teeth.

I manage quite a few properties in those markets.

We manage hundreds of units.

I take a picture of their driver's license.I ask for phone numbers that accept texts and any alternate land or business phone numbers.I ask for the names and birth dates of anyone under 18, and ask if there are any service / emotional support animals, together with their names and breeds.I also ask for personal references, previous landlord contact info (and length of time there), employer contact info (and how long there, together with earnings), as well as the name and contact information for their manager / boss.

Here is my method I got that has done me wonders, I used the method from Brandon Turners book on managing properties:1.)