I never thought about joint a management company though.

I'd like to plan a lot of the build myself but also looking for experienced contractors (architects and other trades) who can help with it.

There are companies that perform this as a service.  

Real estate tends to be balance sheet heavy and you want a bookkeeping company that specializes in real estate.

There are a few Home Warranty companies such as American Home Shield, First American Home Warranty, Choice Home Warranty, Old Republican Home Protection, just to name a few. 

Just know that this is effectively what you are doing.First of all, see if electing an S-Corp for the management company is right for you. 

Yeah to be honest.. similar to a LTR. once the systems are setup in regards to documents, listings, cleaners, handymen, trades etc.

How did you find your lawn maintenance company?

While demolition costs are nondeductible, a taxpayer may claim a loss deduction when the depreciable business property is retired from use in a trade or business or from use in the production of income.I would strongly advice talking with a real estate focused accountant here to help guide you.

Yes, you're scaling now but more importantly, you can truly stop trading time for money and and start living your life on your on terms while building generational wealth for your family.