HereForTheBeer: The wife wants to move out of town and get a place nearby in the countryside, maybe a couple acres (4,050 m-squared is roughly an acre). I can't decide where I stand on this: I'd like the space and it would be helpful for my business stuff to have a dedicated shop on the property, but I also like our little village and this house. Not looking forward to the fix-ups necessary to help with selling the place, but we are planning on doing much of this stuff anyway in the event we decide to stay.
Just not thrilled with the idea of moving again. I had my fill of that for the first ~35 years of life (about 15 different places over that period) and was hoping this would be the last time.
Having grown up on places just like that you may be grossly underestimating the obscene amount of upkeep places like that need. Do you own a walk behind snowblower? A large (small farm sized) riding lawnmower? You may need to with a place like that. Will you end up with a small orchard or "garden"? Yeah, kiss a couple of weekends every year good bye working on keeping that up (though the fruit is tasty). You may also need a rifle and a barn cat (not the inside kitty-cat, the mean, outdoor kind, that will eat rats and other large pests), two things you may or may not want. Also, usually there's at least one structure in poor repair on those places (barn, house, shop, or garage) that will take you a year or two to put right, that always sucks too.
I'm with ya, moving sucks, especially if you're plenty happy where you are. I've been trying to "downsize", not upsize, myself. I don't need tons of space and I really don't need most of my "things" to be happy. The more I get rid of, the happier I am. I'm also happier walking to work, biking to the store, etc., rather than driving. I may be able to simply get rid of my car in another year or two and just rent one for an occasional trip.