Lastly, are all entities required to file tax returns and does this structure, notwithstanding the liability advantages, seem overkill? 

I personally think that he is taking advantage of the system.

Personally, I like to keep mine on a MTM after the initial lease expires because it’s more advantageous for the landlord and I can raise the rent more often than once per year if needed.

I've always had an entrepreneurial spirit inside of me, and I feel like this is the best way to use that to my advantage.  

There are many advantages to what I refer to as "the regionals".

If you have your property under an LLC you cannot DIY represent yourself anyway.Also,  consider approaching your local media outlet or writing a letter to editor of newspaper and contacting your representative government officials to let them know that you are a landlord who has a tenant who is able to pay rent but has taken advantage of the terms of the emergency eviction moratorium and refuses to pay rent.   

I imagine that you'll find both local and other / national lenders that will do it for you if you meet the criteria, but as @Nick Rutkowski said there are lots of advantages to developing a relationship with a local lender.

Right now, inventory is a little compressed so the sellers have a little bit of an advantage IF it is priced correctly.

It can be done; however, there is a lot of room for someone to take advantage of you because you lack experience and do not live in the area.  1) I would suggest you post another forum to ask people who invest out of their home state how they build and manage their team while living out of state. 

I see my age as an advantage here.