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Since you're still considering where to live I would highly consider Ocala. You could get cheap housing with land. It is known for horses and you can easily pick up a lot of accounts there and towards Leesburg, Lady Lake, and The Villages. Those are prime retirement communities.
I have lived in Ocala for 30 years and have been in business since 1998. This is a tuff area to be in business! My yearly gross has only grown 30% combined in the last 4 years and then lost that gain with the loss of one big job last August. Thats is with a lot of money spent on advertising and knowing a lot of people. The problem is everyone knows a couple of people in the business in this county. The only oppurtunity here is in the retirement communities but the pay is ridiculous! Average lawn is $ 45-60 per month in those communities. ValleyCrest and Brinkman have moved in the past few years and really started taking big chunk of the commerical work! Brinkman alone out bid me on $ 150 K a/year worth of bids last year. The unemployment rate is the second highest in the state. If I was going to start fresh it would be here!