Quote from @Rafael Ramos: I’m Rafael, a business owner based in Florida, and I’m looking for some advice to craft the best real estate investment strategy.

Tom, Based on what you've provided, if the property was held over one year, you'd be subject to the long term capital gains rates and any depreciation that you took on the property in the past would have to be "recaptured" (Added to your income) at the short term tax rates (but it will not exceed 25%). 

He is regarded as the STR expert in the area but he has used every strategy in the book, and should be able to point you in the right direction based on your goals!

Even if rents are trending up, if your tenant base can't make ends meet, the asset won't perform.

Ability to repay - can you as the borrower afford the payments based on the loan amount.Typically they will not take into consideration the mortgage on a new property that has not been taken out as that is new.

@Cherie Carr deal machine has an app for that it subscription based.

Based on my experience managing a significant number of rentals, leasing back to a seller can work, but it’s essential to approach it carefully.Lease Start Date:The lease should be signed at closing and start on the same day—Monday in your case.

As a result the property, based on capitalization rates, can now be sold for $450,000.  

Last time in my MFD ( multi Function Display) went off line and I had to break off and climb out of the clouds get on top and go back to home base.. that was a 15k  box that broke :( 

In Phoenix, where I’m based, or in markets like San Antonio, the best realtors do more than just list properties.. they go “driving for dollars” to find oppurtunity, leverage their local networks (probate attorneys, CPAs, divorce attorneys) and carefully analyze each property’s cash flow.