We are as we speak, preparing to close on an Island property on the lake. We had exactly the same thoughts that you are having now. 3 kids, oldest goes to college in 3 years. Our thoughts ended up being that if we don't do it now, we won't and may regret it. We kept our costs down by buying on an island (much less expensive to get waterfront). There are drawbacks, but it was what worked for us to get the lifestyle that we wanted.
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