Additionally - this would be our very first investment property that happens to be out-of-state as well. 

But it's best to jump in feet first.One thing that's helped - I've been able to grow our organizers by three additional people - we have a US / Korea Liason, a bilingual research analyst, and another coordinator.

Additionally, the national debt is becoming a thing.

Essentially at that moment you own them outright and could sell them without additional tax. 

Yes, insurance should be in the LLC's name in this instance and you should also have yourself as an individual and "yourself, Member" listed as additional insureds.

@Nicholas L.Of course, additional rules won't protect 100% but at least something to use if anything goes wrong because my last tenant cost me more than 7K to repair. 

will add it to my template response for why house hacking is better, why it works in expensive markets, and how the goal is not to 'cash flow.'

Additionally, I'd love to get info on the local meetup - I will send you a message direct. 

While Section 8 rentals offer stable income, be prepared for additional regulations and inspections, and thoroughly research program guidelines.

In addition many CA cities have big anti STR sentiment.