If someone is willing to live in and renovate the 2 of last 5 year capital gains exclusion is a significant consideration.

If there's a hole, it may be a red flag.b) sensitivity analysis: I examine all the assumptions, and make sure I can live with the worst case scenarios.c) "Stall and see": if they are getting money over multiple years, and there is no penalty for investing later, I would usually wait so I get some real performance data, versus having to look at theoretical pro forma information.d) Recession stress test: I will not invest in anything, until I subject it to recession level stress and see if I can live with the result.

Convince yourself that there's a better than average chance that you will lose, and if you can live with the time, energy and money spent if you do. 

Quote from @Derek Farmer: Hello all,I am 25 years old living in Indianapolis Indiana. 

Living trust does nothing for anonymity.

Main goal of All In One heloc or 1st Lien Position Heloc:  Lower your daily average balance.Main Drawback: Rates are substantially higher than 60% of current 1st mortgage balances.If you are mostly living paycheck to paycheck and your money leaves your account as soon as it comes in to pay bills, this is not for you. 

Living in the Bay Area.

He wants to live in one and use the other for his studio. 

Find Brandon's videos on YouTube for the "four square" method of analyzing homes and practice.

I specialize in working with Canadians that own property down here (I live in Palm Springs, we might be the snowbird capital of the world?).