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

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.

The time has come for me to start investing in real estate and before doing so i'm looking to build a strong and dedicated team of partners: agents, lenders, contractors and property managers mainly in the Cleveland area (but also open to markets within a 2-3 hr drive away) that already possess an excellent track record in their line of work and that value long term collaboration.

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.

With the way my portfolio and pipeline is arranged I can understand why the construction management or brokerage verticals are most enticing but it still feels too transactional which is what I want to avoid.

I have five houses in Memphis area, and the biggest problem has been finding a good property management company. 

However, I’d like to have a space of my own before living with others again (I plan to house hack again with my next property).I’m seeking advice on how to move forward, as I need to consider things like utilities, taxes, landlord/umbrella insurance, and managing the property, especially with someone renting my garage.Specifically, I’m curious about renting out individual rooms and living on my own for a little while.

Their pro formas felt optimistic with providing 6% annual appreciation and property management that is only about 6% of rent so I take it with a grain of salt (they offer their own property management services but it has terrible reviews on Yelp so I would probably go with someone else). 

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