Why is it a good deal or why is it a bad deal?

That can include roof, water heater, HVAC, plumbing, electrical, mold, rot, warped floor boards, bad foundation, termites, sink holes, fascinating animal occupants, bad reputations (that was a drug house or had a fire or was used for other things that I don't want to mention), and so on.

Be smart and dont lose money on bad decisions. 

Neighborhoods matter, even a few miles can make the difference between good and bad deals.

I have nothing against me, no criminal record, good credit, job, income, savings, single male, no kids... could the HOA decline my highest offer the property to whoever they choose? 

Mostly because landlords have more power and freedom to raise rents and get rid of bad tenants much unlike Ontario.

Hey AlbertoWe have about 70 doors primarily in Tampa/St Pete/Clearwater area but also have some in Naples, Ft Myers, and Kissimmee.We are pretty much the same as you but I will add some caveats from our experience:January - Definitely good the first week but generally pretty bad the rest of the month. 

Unfortunately, this is bad news for me, as I had planned to expand if the first property was successful as a STR.

I have good credit and a stable income, but not a lot of savings.

Look at your expenses- if you have a car payment, credit card payment, etc, get rid of those.