It gets easier with experience.

My experience is that is a kind way of saying "We will add 200 basis points to our quote because your deal isn't normal for us."  

I figured I would invest in real world experience instead of paying a guru $20,000 to teach me what I could learn online.

You don't need to know everything to get started; you need a foundation to build on and the rest will come through experience and then refining your education.You can build a basic understanding of investing in 3-6 months.

I live in San Diego and Im also looking to start investing out of state with little to no experience.

Does anyone have experience in this area? 

I'm playing the same game - Roth SDIRA, although I'll prob start purchasing through an entity as well in the near future.

Once he has some experience, your friend could start a fund and take on investors.

If so what’s been your experience so far?

They will limit the days it can be used as an STR for the 1st year but in my experience they do not follow up to track the actually days.