>I just didn't have enough money to meaningfully invest in the S&P

The minimum to invest in the Fidelity 500 Index Fund is $0:

https://fundresearch.fidelity.com/mutual-funds/summary/315911750

You just experienced the major downside of investing in property when you don't have enough liquid assets to cover unexpected expenses: you have to sell the entire property to get your money out. If you have no liquidity, then that's the position you're in. Remember, there are other ways to invest besides property that are very lucrative, a standard brokerage account and an S&P 500 Index fund being one of them. The benefit is you can sell some of your investments instead of the entire thing to get some cash out.

I would sell the property and put the proceeds (minus what you pay in taxes), into a brokerage account. No debt on that investment either. Pretty big plus.

Your income in no way justifies a truck, maybe a used sedan. Don't fall into that trap.

Because they charge a fee to negotiate the lower balances, so the money you save may or may not be worth it. Check this review:

https://www.forbes.com/advisor/debt-relief/accredited-debt-relief-review/

I don't know what your income is, but $27k is not enough for me to start with debt relief services. Just some good ol' fashioned discipline will work. However, YOU can do the same legwork they would have done by calling the creditors yourself and attempting to negotiate a lower interest rate. Sometimes they will lower your rate for a time period so you can concentrate on loans that did not lower the rate.

You need to get your budget in line and live WAY beneath your means before you play these interest rate games. If you are still racking up credit card debt, then no amount of consolidation will ever help you; you'll just get yourself into a worse situation. You need to stop using credit cards until your finances are in order.

Using the Avalanche method (highest interest rates first) or the Snowball method (lowest balances first), just pay off the debts over time. What is the interest rate on the Happy Money loan? 8.99% interest on a personal loan is far better than typical credit card rates, but if the Happy Money loan is cheaper than just use two loans and pay them off AGGRESIVELY.