I'm not sure if there is a creative way to accomplish my goal through that software that is integrated as well.

I'd speculate that your CPA failed to check the "complete disposition of activity" checkbox in his tax software, keeping these losses locked instead of releasing them.2.

I'm co-owner of a small 2 man software dev shop. 

It seems like the condo you linked is almost geared towards short term rentals, so you should be in the clear on this specific situation. 2) I would take a look at some STR data either via a dynamic pricing software (pricelabs, wheelhouse, etc.) or take a look at Airdna to take a look to see what is the “sweet spot” is in terms of size of rentals in your market.

Theres lots of books, info and software.

It's the only software I have tried so I don't know how it compares.What I can say is it's easy to navigate and they keep making improvements at the request of their user's suggestions.

I was a software architect of a JSF subsystem.  

When you get larger, migrate to a property management software that automates these things.

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I personally think these sheets are better than what I’ve seen on commercial software primarily because I built them from an investor’s perspective based on our priorities.