Your answers are absolute gold.

Non of us, no matter how experienced, have a crystal ball that we can look into and see the future outcome of an investment.

Quote from @Anderson Banegas Cerrato: Tim, this is gold!

And given syndications are a marketing game more than a real estate game, it begins to give you real marketing content to share with the world to help drive new leads for future deals.

My strategy for the foreseeable future is 'buy and hold' with long-term tenants. 

This led me to have an extreme ambition of trying to give my future family the things I didn't get.

In other words if you do the electrical or plumbing repair right the first time it’s highly unlikely you will need to repeat the same repair again in the future.

I would love to make a move before the end of the year and so I keep trying to decide which of the following is best for me:1) Buy 1 more expensive CA property near here, and thus a better tenant (less likely to cause issues), but lose a little bit of money every month due to the current numbers, while hoping for future appreciation? 

This could help protect against any future lawsuits. 

(You know you’re on the right track and you insure future leases end between March and July by varying the length of the new lease.)Good luck.