I personally feel as though establishing a series LLC is the move for me.

Ok, so it's established that no DOS clause exists anywhere in the note, but that the note DOES say that it's not assumable.  

You can learn different trades through establishing a good network of people, but you can also save money on jobs by just taking care of the non skilled trade jobs and only hiring the professionals when needed.A real estate license can be obtained if you feel the need and won't require a large time or money commitment.I personally hold a sales position and try and use all of my variable income for real estate investment and live off my salary.

Can self employed people establish some sort of medical spending account from which to pay obamacare premiums on a pre tax basis?

@Bobby Hughes,I'm not sure what your options are with an annuity that has already been established, but I would ask your financial adviser / annuity account representative if you have the option to convert that annuity to another form of tax-deferred retirement account. 

Again, this is how the lenders think of these - there might not be much logic involved, just rules and policies established over time (likely from having been burned too often in the past).

If you choose to stay in SF to invest,  seek out JV partnerships with other established investors in the area. 

Nothing longer.It's difficult to get Fannie / Freddie loans until you are a little more established, so most people are stuck with 5 year bank loans as they build up the portfolio.

Since you own the properties out right, consider moving them to a LLC, and to further add to your protection, establish the LLC somewhere like Wyoming or Nevada.  

Establishing an escrow will increase the cost of the money but ....