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? 

Expenses beyond debt repayment will be only a rough estimate.

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. 

I also have 0 debt!

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. 

., don’t forget the CPA and Lawyer costs) Again Net Operating Income is calculated before debt - what matters more is the NET Annual Income (or annual cash flow): NET Annual Income = Net_Operating_Income - Mortgage_PaymentsAnd that leads to the Cash on Cash Return on Investment: C/C ROI = Annual Cash Flow / (Down Payment + Closing Costs)And I’m willing to bet you don’t get C/C ROI above 10% on any SFR in Austin area (based on these calculations and bought with conventional means, not subject-to or assumptions, or owner financing or other creative financing).

The reason I side tracked on law school was because I did not want to incur a large amount of debt, spend 3 years in school effectively allowing me to miss out on investment opportunities while not generating any income during that time period.

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.  

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