I echo what others said about checking out the association, including rules and regulations, reserves, etc.

You must ask about children, sex and age, as to be compliant with HUD regulations.

The tenant has been paying $1000 since spring 2010, so I was going to give them a $100 raise this spring, the rent is not regulated.

That state's bank regulation enforcement div will be paying them a call any day now.

They seem to see regulations and laws as restricting their freedom or as nonsense roadblocks.

I can tell you too, that if you need to find someone who really knows HUD leasing regulations, Section 8 rules and or Public Housing regulations, start asking the tenants, I have met several that know the regs better than anyone in the PHA office and most know them at least as well.

What are the current SEC regulations regarding soliciting funding for projects?

If so in my state all formal offers must be submitted to the owner within 24 hrs, there is likely a similar regulation where you live.  

I don't dare landlord in SF with all the rent control and landlord hostile regulations.

If you are going to rent by the room (or two to a room) then you may fall under boarding house regulations.