Those are questions you need to answer.Also, just because they finally were raised to market rent (or close to it) does not mean that they deserve a 'present'.

This was a conference for mostly private equity firms that raise money for and invest in large multi-family deals, and truthfully I felt a little out of my depth.

And you risk the boy friends and baby daddy's.. that's your risk.And of course kids are rough on houses I don't care what environment they are raised in.. 

The Quit Claim Deed raises the question why? 

You wire funds to a company that is in the business of building buildings, they create plans, get permits, raise additional capital, supervise construction, supervise filling the building with tenants, sell the building to an institutional investor, and if everything has gone to plan then there will be a significant profit and they wire you back more money than you put in.

Most don't have any experience at all and are using my property as a test case.

WA, for example, requires that you take 20 hours of state-sponsored classes and pass a state-sponsored test.

I’d look at how long you plan to live there first as the longer you live there typically the higher you can raise rents organically due to inflation and the overall cost of living increasing every year.

I don’t think his parents did a very good job in ensuring he wasn’t being raised with entitlement issues!  

Poor insulation and single pane windows will raise that cost to run the furnace quite a bit so you might want to see where the break point is for upgrading.The biggest issue is power outages in the winter.