CA has more than half of the nations homeless/unsheltered persons. 

@Lauren MerendinoI strongly believe that your chosen market should be somewhere that you can go to in person / have strong personal knowledge of / have family or a network in already.  

I haven't personally dealt with any crazy insurance premiums such as the ones people have been advertising in like Tampa, FL.

It's not a personal sale between you and your son, but rather a sale from one LLC to another.

Choose a goal so ambitious it forces you to grow into the person who can achieve it.

If you have a chunk of money to get going I'd personally buy the biggest thing you can if you don't I think house hacking into a 4 plex is great. 

I want to exit as I don't get any personal use from the STR being 20 mins from home and would rather apply the capital to another opportunity in multifamily (LTR) or another STR in Hawaii where my brother is a broker and now manages STRs.

I would start close to where you live personally. 

People want reliability, honesty, being on time, and having a good personality more than just a few $$.

Take into consideration that when the person you gifted the property to will have special tax considerations as well