I may be partial but seems a pretty obvious top 5 choice. 

If I can do a cosmetic flip and have the crews that can knock it out in a few weeks so we can relist it and do three in the  time it takes to do a full rehab which will have my money and attention tied up for months, the simple flip would be my choice. 

Technology makes long distance investing possible, but it's still easier and less risky to do it close to home. 

I’m expecting 2.5 to 3k rent. should I assume that I will get stable and easier tenants?

For a lot of investors Orlando is a really poor choice. 

Some of the calculators are just more robust and from feedback sounded like it would be easier to navigate through a desktop version. 

It used to be called TurnoverBNB.The cleaners on there understand (I hope) STR turnovers and methods.In that area you should be able to find more than a few choices.

After a set amount of time, you get the choice to complete the transaction (buy the house) at the agreed price or not buy the house and the owner keeps the extra amount of the rent payments. 

That might have the best quality of life component based on what you described.Not sure if you have a financial advisor, but I've found mine is incredibly helpful in narrowing down big choices like this.I hope it works out great for you!

For those of you facing similar choices, what key factors influence your decision to hold, adjust, or even divest from properties here?