With a calculation being on a deal by deal basis you'll need to go in depth with costs VS profit with both scenarios and timelines. 

Ultimately, my question was asking for referrals to an excellent financial advisor who I can go into more depth with.

Once it's determined that a property is eligible for STR usages, an in-depth analysis and Pro Forma should be developed with help from online tools and estimators (such as AirDnA), real world rental experience, local PM companies, lenders and RE Broker.

Obviously there would be a more in-depth analysis if I were actually buying the property. 

They didn't go in depth as to what exactly that meant but it's safe to assume they want to help a local family make it their primary residence.

I knew of realtors/investors that committed suicide due to the depth of the financial hole that they found themselves with Miami condos.

Feel free to reach out to discuss in depth!

I do specialize in all of middle TN so let me know if you would like to connect and we could get a little more in depth. 

Then you can read a more in-depth book like The Book On Rental Property Investing by Brandon Turner or The Unofficial Guide to Real Estate Investing by Spencer Strauss.2.

Then you can read a more in-depth book like The Book On Rental Property Investing by Brandon Turner or The Unofficial Guide to Real Estate Investing by Spencer Strauss.2.