My wife and I have also thought about the acreage thing (but work in the city), very seriously. But frankly (for us) the time alone is the largest deterrent. We enjoy our summers (camping every weekend), and I notice that you do also, that would definitely take a backseat to your acreage upkeep. While "the grass is always greener", just make sure you realize that everything will now take longer. Commuting/groceries/running to the store/cutting lawn/etc.
You say your son just graduated high school. Have you taken into account another reliable vehicle (for your son), what about post secondary? From my experience of having to spend 1.5 hours on City transit each way when I was in high school & college, the last thing I would want is my parents to move farther out.
Trust me, I completely understand the pros of an acreage (space alone is the biggest plus), just make sure you understand all the cons.
In our eyes, the vacation property will be a better idea (but we also have toddlers, so time is limited as it is).
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