First, have a conversation with an accounting firm to see if a cost segregation study will be beneficial to you.You don't want to spend money on something where you won't get a benefit from.

Also @Tim Phillips something to be aware of in FL, all condos older than 30 years and taller than 3 stories are required to have a "Structural Integrity Reserve Study" performed before the end of this year.

Aloha,For comparing Condos/HOA projects for investment purposes, the more critical info would be rating the most recent Reserve Study and/or Reserve Funding Plan for a specific project.

I realize that a full feasibility study will most likely be required if I move forward with an LOI and purchase contract.

I guide clients who are looking to treat their STR as active.Somethings to consider are whether you should get a cost segregation study done, creating a log of your hours and having an understanding of what hours count / don't count.

I'm one of the case studies in the BP book, The House Hacking Strategy. 

Document your experience so you can share a case study here or at your local REIA

There was a case study where a GP raised a million dollars for a deal with 70% of the funds coming from his personal network. 

Study their pricing, occupancy rates, amenities, and guest reviews.