As the regulatory landscape has gotten more complicated during COVID-19—with a halt on evictions and late fees, as well as other local laws being passed to help keep renters in their homes—property managers and their knowledge within the market, ability to maintain profitability and tracking ever-changing legalities are even more valuable than it was a year ago.If you've owned income property for any length of time, you know that managing a rental can be financially rewarding.

But I think that the rules regarding licensing for Property Managers in your location will inform you of the answer of your 1. question.I would recommend seeing if your state has a DORA like we have in CO (Department of Regulatory Agencies > Division of Real Estate).

You need to study basic business law, taxation, regulatory issues like Truth-In-Advertising, the Fair Credit Act, aspects of the Uniform Commercial Code and the rules that are applied to business that apply to all business activities, not just real estate.

First, the regulatory costs (legal, SEC filing fee, etc) are not crazy.  

As for leases, I don't know where I actually file them other than making copies for both parties and keeping a copy for our office for regulatory reasons.I'm not saying that having a Realtor is "bad," but in reading your post it sounds as if Realtors are taking on more liability than they really are.

You get points for creative thinking but this idea isn't very practical in today's regulatory environment.

I was wondering what kind of issues to expect from a burn situation - things like water damage, permits, blueprints, regulatory compliance, etc - that sort of thing.

I could very easily imagine that folks would go on vacation far less often or not at all during a recession for example, so I'd expect your vacancy rate would be much more cyclical ... that and the regulatory risk of the city effectively outlawing it ... 

Some small non-profits serving a niche may obtain free or subsidized rents from a United Way.If you want a nursing home or such, find an existing provider and lease to them as trying to get into that business is haunted with stiff competition, regulatory oversight and it is very political as it is based on community needs.

The cost to generate a conventional loan in all the vendor and regulatory add-ons is between $3000 and $8000.