It should be a tool used by experienced parties in specific scenarios.

The committees have never said they'll require a specific form of evidence to show that you've rented the place for at least a couple of nights.

Are there specific states or locations you’re looking for?

Curious how this will play out in the courts (granted it's LTR) and affect pricing products used for STR such as PriceLabs (which I use but have to seriously manually adjust for very specific reasons).

Is there any specific area where you could use some support or advice?

If you are looking to build connections specifically in the DFW metroplex I have been hosting a monthly meetup for the past 3 or so years, id love to connect and get you some more info! 

One workaround could be keeping a separate spreadsheet to track your adjusted tax basis accurately and only using Stessa for operational insights.You could also reach out to a cpa and see if they have a specific recommendation for software to use.  

Here are a few additional strategies that might help mitigate risk if you decide to rent the property:Hire a Strong Property Management Company: While you’ve already spoken with some PMs, consider finding one with extensive experience managing single-family rentals in Cook County specifically.

If the tenant fails to provide proof, I would reach out to a local attorney about handling the lease violation appropriately, especially since Texas has specific landlord-tenant laws.

However, I agree with you that I will never again work with that specific attorney again.