John,
You will have no problems purchasing a 2/2 overlooking the intracoastal in Treasure Island . However, you need to know that the rental market now is becoming saturated. Because our sale prices have declined in the last years, many sellers are pulling out rather than continuing to lower their price, and doing the next best thing which is renting their property. Therefore, there are no guarantees that you will be able to rent your unit. Our best rental season is from October to mid April. That is when we have the best weather and when we have many tourists from foreign counties. If you are serious about buying now is definitely the time. Prices are affordable, and the inventory is high. Just remember that you may , at times have an empty unit..
If you have any questions, please call me at 727-455-8266. I would be happy to continue this conversation via telephone.

Hey John,
The amount of time you can rent is determined first by each condo community from weekly to annually. Most cities default is 30 day minimums.

The hottest rental market here is from October to March. Many have 180 minimum rents to avoid 12% bed tax ( like hotels) - we specialize in helping buyers in our beach areas and can give you access to free tool to research what's on the market. I can help you determine the condos that meet your rental requirements as well as your purchase requirements.

Email me at cyndeehaydon@gmail.com or call us if you'd like more help.
P.S. You may want to check out our client video testimonials too.