I’m seeking advice on a difficult financial decision. My fiancé and I are both in our late 30s and came into our relationship with a sizable amount of debt from past divorces. I (F36) own two rental properties—one in Hawaii and one in Washington state—that I brought into the relationship. We recently purchased a new home, and since we used my fiancé’s VA loan, only his name is on the mortgage.
While our relationship is strong, the biggest stressor is our combined debt. We both make good money and can manage our bills and debt payments, but if we could pay off the debt, we’d have an additional $8,000 per month to save and invest. Recently, my fiancé suggested selling my Hawaii rental property to use the $150,000 in equity to pay off our debt in one go. The renters cover the mortgage, but I’m in the red by about $740 a month due to the HOA fees, which are relatively low for Hawaii.
His argument is that paying off our debt now would allow us to save more money and potentially buy another property in Hawaii in the future. He’s also agreed to put in legal writing (via a prenuptial agreement) that I would either be added to the mortgage when we refinance or be entitled to half of the profit if we sell the home.
I’ve always viewed my rental properties as long-term investments that will contribute to my retirement and provide passive income. While I’m currently about $900 in the red each month across both properties, I believe they’ll pay off in the long run. I’m torn between the immediate financial relief of paying off our debt and holding onto an “economy-proof” property in Hawaii that could be a valuable asset for my future.
What are your thoughts? Should I consider selling the property to pay off our debt, or is it wiser to hold onto it for long-term security? Any advice would be greatly appreciated!