If it isn't, sell and hopefully pocket some profits to invest in something else.If it is for you, you could repeat the process and buy another owner-occupant property and rent our your previous.

If I can't manage remotely my next plan was to hire a PM company to handle things.So far when doing my research it sounds like you can own a STR in San Diego in their "Tier 3" category.

So, if your sub2 seller declares bankruptcy ... and you did things correctly, you have a very short period of time to refinance.If your sub2 is not done correctly, it will be tied up in court you will have to hire a lawyer.

I’m in the process of stocking my tool belt with all the knowledge needed to take full advantage of my assets. 

I am in the process of researching this subject. 

if your goal is cashflow, but you don't want to self-manage a STR or MTR, then selling to make that equity work harder for your somewhere else is the only thing that makes sense. q: would your time be better spent focused on flipping & letting that rental break even, or going through the process of turning that equity into cashflow via a 1031? 

I do have a handyman, but it can be time intensive OR money intensive as I hire someone to run something over to the guests and have to pay them to do it.  

You will need to hire a GC.

You don't want to a rookie do work for you, you would certainly not hire yourself!

If you are comfortable going through the building process and have a builder that you trust you would probably get the best return by building on the lot and then selling and deploying that equity that you have now built into another asset via a 1031 exchange.