My endgame is to end up with $300k/yr in post-mortgage income in 20 years based on investments I make now followed by continued investments over the next 10-15 years own.

Unless you have a clause in the purchase of the entity that clearly makes you responsible for the entity from the day that you buy it(Indemnification) I wouldn't bother with the LLC.Good luck man. all the best!

The parking for the ADU will run along the side of the primary w plenty of space for back to back cars.

I was studying the market and my rent will be just enough to cover the mortgage and HOA fee now I might to pay out of pocket for insurance but don't want to sell it yet because the area is growing and might have good appreciation in the years that follow.

Any tips or advice?

Feel free to ask if you’d like more tips on what to look for in a PM. 

It depends on the experience they've had.

Also any tips for automating this as much as possible and how to protect the property financially and property management would be appreciated.I ALMOST understand the rental arbitrage strategy if building a company scaling with say 30 + units and looking for high short term cash flow.  

@Brian Rocha It’s clear why most lenders insist on including rehab funds in the loan, and all of our partner banks follow this practice for fix-and-flip loans to minimize risk and meet securitization standards.

Just wondering can you ever catch a great deal on the market  and if so what’s stopping you from taking advantage?