As for the numbers once I move out, I don't feel comfortable continuing to rent by the room with separate leases and constantly having new people in and out (of which may not know one another).

I’m really struggling on crafting the appropriate rental agreement and wanting to provide a level of separation and degree of confidentiality between his roommates, mainly to avoid any potential interpersonal conflicts.

I've heard it is preferable to have separate contracts with each building professional (architect, engineer, contractor), but why?

From what I understand, if the land is split into separate parcels, I can avoid it being considered a Park and not have to worry about all the red tape.

Separate trusts/llcs or a single holding company?  

I got overwhelmed by the sheer expense of calling separately a plumber, electrician and carpenter for different jobs.

23 separate STRs with about 75 televisions. 

This increases your taxes, not decreases them.If you're talking about having rental properties, and you mention GC in the context of exclusively doing your own rehabs - your separate GC business has to have an intention to make profit and operate accordingly.

I also use them during vacancy turnovers since those turnovers are fully automated, self-serve showings, but you have to have a way to ensure batteries get swapped out regularly, then run a separate cellular network to push updates to the locks over time, which is a another added cost.

@Bernard SangaStandard/itemized deduction are separate than deductions are they relate to your investment property.If you brought an investment property - you should interview your accountant if he is familiar with tax laws as they pertain to real estate.