I'm also quite certain he has an alcohol issue, as I always smell alcohol when we speak in person.When the tenant first moved in, he would wait for my wife to leave for work and then rush outside to talk to her, often presenting significant problems he was facing – hospital visits, sick parents, cyber hacking, and more.

Don't parent. 

I know stay at home parents that get it, just in case a friend or family member wants to buy or sell.  

The end taxpayer (the parent LLC) was the same for all transactions, so even though there were three separate names on the deeds, no moving of deeds around had to happen.

My parents loaned me money twice and it worked out fine.

If we were to sell, we're looking 1.2-1.5mil.Our situation is we want to purchase another property for my parents to live in - it would be 600-700k condo.

There's software that can tell even which blocks has the highest appreciation per zip code. this is for rehab or buy-and-hold long term.The inside factor that really makes higher appreciation is good school districts as parents wouldn't need to pay private schools for their kids. 

@Andrew Stouse, continue living with your parents while saving for closing costs/reserves.

As far as utilities go many years ago my parents owned a 12 unit apartment complex that had all shared utilities.

Once everyone is clear on the big picture of what the estate plan is and what your parents want, other issues dealing with specific properties and specific issues such as 1031s, shifting to other investments, financing issues, etc. will become clearer.