Both properties are zoned RH and could combine to create about a 9,600 square foot lot.

If your friend wanst to create a somewhat segregated space for a long term roommate inside the residence I don't know that the HOA can really do anything about that without violating federal law...

This is why you budget and create a reserve funds.

Many lenders will vary their programs to create niches for customers and remain competitive. 

Long term game, we are looking to really target multifamily properties for long term wealth accumulation and cash flow, but I don't see how that could even be remotely possible in the CA market without substantial starting capital.Some of my other thoughts creating our indecisiveness include:-Despite the amount of research and networking we do, would out of state investing for a beginner not be advised?

Can I do this if I put the property in an LLC I create specifically for it at the purchase of it? 

They are jobs.If you want to create a low effort income stream (I would not refer to even buy and hold RE as truly passive) then BRRRR is a good approach. 

If you don't have one, create a bigger pockets meet up! 

I would love to be able to become completely debt free within the next 5-8 years (or less), and then focus on creating some long-term passive income.

My suggestion is to stop looking for a "real" job and start creating your own.