Here is a CSS Decision Diagram flowchart intended to bring together all the various questions when assessing the benefits of a Cost Segregation Study (via a professional or DIY).

Hi, Stephen - not sure if you ever pursued learning more about midterm rentals, but I'm noticing from the conversation thread that there's some incorrect or misinformed information in some of the comments.

At which point I can make a more data driven decision. 

AND rush you into decision leaving very little time for you to investigate the risk involved with this request.My VOTE, proceed with caution.

Is property owner the sole decision maker So, as you can see, all real estate advisors recommend getting the most information possible and then trying to structure the transaction in a way that provides for satisfying at least some of the seller’s needs, wants and desires.  

You want an accountant that can help you strategize and who is responsive when you want to know the tax consequences of the decisions you are making throughout the year.Good luck and let me know if you have any questions.

His advice on improvements is incorrect for Alabama.

I've always been curious on this one as I run into a ton of folks that did taxes incorrectly on turbotax/h&R/etc...and for the question, I think reaching out to a local CPA or to Michael above and just paying for it may be far easier than trying to deal with the IRS yourself.

Lots of great educators on youtube for getting data to drive decisions.

@David Colthart Great decision David!