Return:Finishing the basement and adding bedrooms can add significant value, especially if your local market places a premium on additional living space.

Additionally, I was not making enough from my corporate job to support any kind of significant mortgage payment.

Given that you're not married, that adds some additional complexity.  

It'll take time but can really pay off if you stick with it.I'm in Los Angeles and I've investing in TN and GA in the past, and currently investing in SE Wisconsin (your area).Let's connect and discuss the market.

That higher interest will be a lower cost than the closing costs for the refinance so a net gain (depending on your new loan size). 

I would have contacted the locksmith tech to get additional details before assuming it was tenant damage.

Quote from @Shaun Ortiz: Hi Jason,Thanks for sharing your journey—it sounds like you’ve gained some invaluable insights from your experiences, even with the squirrel tenants (that’s definitely a story!).

I know this is a very old thread but if anyone comes across it I wanted to add some additional thoughts that might be helpful.

For example, I see newer investors attempting wholesaling or bird-dogging for other investors to generate additional income to invest.

Also demand proof of insurance from tenant as yo insurance and add you as additional insured.