Some mortgage brokers gave me mixed and unclear answers that "its probably not a good idea".

But as you said, new tech allows you to auto set them at 7pm or 8pm and turn them on at 6am.

Surprisingly to me, Santa Clara County had mixed indicators, only marching up 70% of the way to historical unaffordability from the most affordable watermark.

I'm pretty tech savvy.

Not until J Scott and Bob Bowling are in the mix ;)

While we don't have (yet) the burial sites, we have a unique collection of 60's hippies that (still) love communism, and hate tech, progress (no idea why they are called "progressive") and success (especially landlord and real estate success roils their blood :)  Add to that an extremely incompetent Bored of Stupidvisors which has a nack for passing local rent control legislation that gets ruled unconstitutional in superior court.

My ROTH IRA account has a mix of dividend paying stocks and momentum stocks.

Mixing family/friends with real estate can be problematic when things go south (been there, done that :-( 5. 

They are super tech savvy.Founded in a Leawood, Kansas in 1961 by Paul Robinson and Joe Gilbert, Houlihan’s is a restaurant with music and creativity in its veins.

My thought would be take the proceeds and put it down at 35% equity on a small strip mall or office/mixed use property.