[allus70]

I just retired, my wife is about a year or so away. We live in NY, though we just came home from a visit to The Villages. This is the place that we want to retire to, pretty certain about that. Here's the part that got me waking up at night.
We found the type home we want, a CYV, in the place we want, within walking distance to Paddock Square and Eisenhower recreation center. It's essentially the same house that we passed up at Mission Hills a few years back and is now about 100K more expensive.
It's going to take a while to sell our home here in NY, and we don't have any firm idea as to what we might get for it. Also, after 5 kids and legions of dogs and cats, it needs work. That means if we buy, we will be paying the bills on 2 homes. If we rent the new home out year around, and I don't think that is likely, correct me if I am wrong, the rent would only cover about 1/2 the costs. Found out were approved for the mortgage.
We are torn between once again between missing out on our dream house, or taking a financial leap of faith and juggling 2 homes. Another consideration is that the 2 homes together would mean being on the hook for almost $500,000 in loans....not exactly the way I wanted to go off into retirement. There's one more detail, though. The Mission Hill's CYV's appreictiated in value when resold, and not necessarily due solely to updates.
Maybe I'm not seeing the whole picture, maybe I'm overlooking some important details. If so, or if your own experience can add some insight to our dilemma and help us decide, please let us know. Thanks