As far as IT Jobs are concerned Orlando, FL might be your best bet professionally in Florida. There is a growing Technology sector (The city seems to be reinventing itself as a Tech center after the Real Estate crash) According to Forbes its the 3rd best city for IS Jobs. (
In Depth: Best Cities For Technology Jobs - No. 3: Orlando-Kissimee, Fla. - Forbes.com)
Here are some other articles:
40. Orlando - BusinessWeek
Wired 15.01: 10 Top Tech Towns
10 Best Cities for Technology Jobs & Entrepreneurship | Economic Edge
You are close to many Lakes and about an hour or so away from the coast for beaches. Sport Bike riding is pretty enjoyable in the area as well, I lived in Central Florida for a while and owned a GSX-R 750 and found some nice rides especially on the back roads towards Daytona Beach.
With that being said though personally I was not a fan of Orlando (I also lived in Toronto for many years as well ironically) and would move to San Francisco if I was involved in IT, but cost of living would prohibit you from achieving your goal of owning a home outright. And plus this isnt about my preferences so who cares really
Orlando would fit exactly what you are looking for, and housing deals are definitely there for the taking as well.
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