I stopped using Craigslist a few years ago because there were so many issues with ads being stolen.I think how much rent you charge MAY play a role in the quality of the tenant you get. 

Sounds like they want to play the game, "Watch the Market Cycle" and buy another place if things cool down.Unless you have tons of assets to protect I wouldn't worry about renting to a lawyer.

Just to play devils advocate - It may be worth looking at taking the tax advantage of living in the house and not taking any capital gains tax when selling and capitalize on the current crazy market and go buy some better cash flowing assets in areas less expensive with better rent to purchase ratios.

If you take cash out beyond purchase price there are other rules that come into play. 

He's not naive to think there wasn't more wayyyyy more at play, but rather that this was a contributing factor that added fuel to the dumpster fire.The US Population growth % has been declining since the 1990s so it's not totally new, but we've been able to shave off less births with immigration.

Additionally, your goals will play a big part in what you ultimately decide.

I call this playing moneyball in real estate. 

Couple tax related questions:1) A 1031 exchange would never come into play in this scenario since there's no actual 'sale' taking place. 2) If we did an actual sale instead of a transfer, could he use a 1031 exchange to pay off his RV and pay no capital gains on the difference between the sale price and the $88k he bought it for 30 years ago?

But not ethically or by law.It is possible that the seller instructed the agent to take the best offer above $XXX,XXX and not to play bidding games. 

I played around with various scenarios in interest rates and generally, I don't see negative cash flow until interest rates increase 3.5% in 5 yrs which is double today's offerings.