I think I've hit analysis paralysis stage with 1 property in my rental portfolio and would appreciate some financial advice, specifically - based on the numbers, does it make sense to hold long term, or 1031 into something better? 

When I do a flip it is for a specific financial purpose.

Congrats on the decision to make real estate a part of your young family's financial plan. 

The answer is likely two-sided: 1) Your income and financial situation determines how much you can actually afford to spend on housing, and 2) You find housing that fits your needs and shop around for the best deal. 

Real estate seems to be the best vehicle to financial freedom, and to allow the time for more meaningful work such as volunteering or being more involved in the community.I've reached out to a few local investors to make some connections, but hope to continue to expand that circle. 

The way you have it set up now according to your description, it isn't going to protect you if your tenant sues you. 

If you think you’ll need to invest additional capital in them in the near future then you should make sure you know exactly where that money is coming from before you buy the property since your future employment is in question.The bank will look at your current financial situation, but they don’t typically inquire about your future state.  

Once you have removed the doubt of a previous owner wanting to get their property back by saying the county didn't handle things to the letter of the law, then you can get title insurance protecting your 100% ownership then sell like any other property.If you have a lot of old owners or bigger problems the the quit claim deeds from the people you can find will help speed up a Quiet Title Action.

I would have switched property management companies after the second financial issue. 

Also how would you create protection when purchasing in a depreciating market?