As tax season is right around the corner, is it better to wait until after I file? 

We kept most of our stuff in a local storage unit.

When I get stressed (which happens to newbies and seasoned investors alike), I try to take a step back and remember my goals and why I'm doing what I'm doing. 

There are plenty of portfolio banks that would be happy to lend you money, especially since you seem like a seasoned investor.

Right now the current tenants have access to it for “storage”.

maybe thru the spring, so you can put the house back on the market come "buying season". for me if i was in your shoes, that's how i would go about it. however a few things that are variables, what are your current financing costs?

I work full time for a community bank in their commercial loans department, B.S. in finance, and bartend nights (just entered out slow season, so I’ll have more nights available).

Keep on truckin' through the slow season BNBers!

Last tax season I am almost certain my taxes weren't done properly in regards to my rental property (ie. expenses for renovations weren't factored in, I paid my taxes well into 2019 due to issue with getting the bill so they weren't factored in).

You might find more options if you open your strategy a bit to bigger multifamilies or self storage.