If you want a prime view lot, then there is most definitely a lottery involved. Interior lots on the other hand are a dime a dozen and there is no competition for those.
I have recently gone through the process, except I purchased a spec home (larger, with an oversized view lot in a prime location) rather than a lot. I bid on and lost six homes before I won one. It took a few months of bidding and losing. I did not sell my existing house first before buying a new one, and probably won't sell it. I'll just keep and try to rent it (although the rental market isn't great either).
If you don't mind moving twice, and owning two homes would be a financial hardship, then selling your existing home first is of course the financially safest route.
I think the village of Charlotte is a nice location, and I bet if you price it aggressively your house will sell. But, like you, I would be skeptical of the Villages appraisal. I am sure it is an honest appraisal, but if you price it there what would be the advantage that your house would have over all the other similar houses that the Villages has appraised?
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