To Pay Down Debt or Finance Future Investments....??

[Benjamin Small]

Hello Everyone...

Financial matters can be such an emotional decision. I have some cash savings along with a modest investment property and a primary residence. I own both properties outright with no mortgage payments. I am saving in a 401k for retirement as well. What I do owe is student loans, and I would like to pursue a Master's degree this fall, which will cost almost $20k over the next two years. A portion of the student loans are private loans through Navient, formerly Sallie Mae, and the rest are federal.

I have almost $20k in cash sitting on the sidelines waiting for the right opportunity.

I could potentially pay down a significant portion of my student loan debt right now, that altogether totals over $60k. I could rehab a property and either rent it out or sell it after the rehab is complete. I could also pay outright for my schooling come August and avoid getting any more student loans.

My main hope is to free myself from the rat race as quickly as possible. I want to pursue an advanced degree so that I can teach in college. I keep my expenses low and I am generally happy with things that way. I want to own a multifamily property, or several, which have some solid cash flow and not depend on a full time job to sustain my expenses.

I am emotionally torn between paying off student loans and holding on to cash and waiting for the right future investment opportunities. I am not quite sure what I would like to do and wondered if anyone had some thoughts.