Make sure to keep your eye on the prize and do not spend too much time chasing after the next hot thing.

Currently, I have a weekly check in with my current contractor, but alot of time it is a chasing game.

Have you taken the time to search AirBNB and VRBO in those specific areas to see how many STRs are operating?

I'm not sure I would get to cute trying to squeeze every time out of it now with a lease that might cause you issues in the future, but the scenario you describe is common and probably smart. 

(make sure you are budgeting for maintenance and management if you plan to use it) Rent will increase over time and your property will continue to appreciate in value. 

@Alejandro Martinez I'm a fellow Canadian from just down the QEW from you (Hamilton) and moved to Orlando just over 5 years ago to invest in real estate full-time. 

The process takes about the same amount of time since an appraisal and title work is generally still required before underwriting and funding the deal. 

There are people who buy a longer term (12 months or more ) OPTION giving them a RIGHT to purchase a subject property, at a certain price, within a certain amount of time, and attempt to either sell the option for a higher price or close on a simultaneous purchase and sale to an end buyer paying a higher price.  

Be first position until he gets the construction loan, at that time he then will have the construction loan buy out his PML out an pay any accrual interest and origination fees.

@Chris Lin,Thank you very much for spending time with me on the phone last night.