One thing we do as a human is speak at the pace of those we speak to or are raised by. 

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 contractor took 3x as long, raised the budget by 70% as kept finding new little things it needed.

The Quit Claim Deed raises the question why? 

And if the numbers are ever that great to where I want to sell a few to raise some cash, I'll either refi and pull cash out or I'll just eat the recapture and take the hit. 

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.

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.