I got a good deal on the house, but do not want to invest in it if I would be out of compliance with renting regulations.

There are also very strict regulations on who can invest in the stock market.

My guess is 2 months' worth is to establish reserves, and the rest is prepaids on these.

Its seems many pros are burying their heads to the regulations or not thoroughly understanding how to interpret STRs in the tax code (the transient rental rules etc).

Your SOW, challenging projects, expensive stuff, can be tricky unless you have experience and an established team. 

If you manage homes built before 1978, there's a key regulation to be aware of: the Environmental Protection Agency (EPA) requires property managers and Landlords Nationwide to be certified in lead-based paint handling.

I loved being a landlord and felt good about it, but since its gotten to be so regulated and anti- landlord here, its best I get out.

You're absolutely right—some investors still flock to cities like New York and San Francisco, even though these places come with more tenant-friendly regulations.

Per fair housing regulations, I can't answer this question. 

Biggest pati le is getting approved from VA and bringing property up to regulation.