There are two places on Indian Trail (I believe) that are cool spots and good surfing at 16th.

It's not like you can hide.It's much easier to invest in an area that wants you to invest, like Indian Rocks Beach, Indian Shores, Largo, unincorporated county, etc.There are 24 municipalities in the county, each with their own laws, some have varying zones within them regulating turnovers differently.Pinellas County itself doesn't have strict laws at all. 

I see Texas, Colorado, Tennessee, Denver, even Indian but I dont see a lot about Chicago IL investor making investment. 

Joel  - At those prices, are your properties in either Waterloo Village or Indian Town?

I work in Vero Beach, Sebastian, and all Indian River County. 

Anywhere in the world, especially in Asia, the price of real property is skyrocket as a hedge and safe investment to a rising gov. printing money/inflation/etc.Ten years ago average people can still buy houses in California,Shanghai, Mumbai,Singapore, Jakarta,London.

No noise,could picture Indians walking across the field.

Single Family Home is going to be better than any condo situation from my experience.If you are looking in southwest FL area by Tampa, Bradenton, Indian Rocks, Cape Coral I could help with your search.

A good example of this is "Indian Village".  

It has a ton of areas that fall in the price-range you mentioned both close (walking/biking distance to beach - Treasure Island, Madeira, Indian Rocks, Gulfport, Pasadena) and further from the beach (10-20min drive to beach - Downtown St.