We moved from Riverwoods on the North Shore from a similar-sized house as yours. Your description of your "stuff" and what you like to do sounded like an echo of our situation. Here are a few tips I'd recommend...
- Pick out the model that you intend to buy in The Villages and carefully lay out the furniture you'd like in each room. What's left uneeded in your new home has to go somewhere, I'm afraid.
- If your furnishings in Chicago are "heavy and ornate", make sure that you really want that look in your new semi-tropical home in The Villages. If you can't picture dark, heavy and ornate furniture here, then unfortunately maybe all your "northern" furniture has to go and you'll need to refurnish here.
- Get rid of most of your clothes. We live in casual clothes, shorts, and maybe a light jacket down here. You might want one dress-up outfit or a suit for special occasions here. Bring one coat for any winter trips north. Otherwise, you will seldom need it. Be very careful. The closets in almost all Florida homes are a fraction of the size you're used to in a big house up north. And there's no basement for the overflow!
- Winnow down the contents of your garage up north. Even if you buy a model with a stretched garage here, two cars and a golf cart will fill it pretty well. You might look for a Villages house with a golf cart garage just for the extra space.
- Consider what you think you might want to store in an attic or garage down here. Don't forget that Florida garages and attics get very hot and very humid.
- There are lots of other tips, but the best story is what happened when the florist delivered a flower arrangement sent by our son a day or so after we moved in. The delivery driver was laughing as we opened the door. He said, "Now you'll need to do what everyone else who moves from up north does." "What's that?", I asked. "Find some air-conditioned storage space for the stuff you don't have room for.", he answered. "And then, after you get sick of paying the storage bills after a year or so, you'll get rid of all the stuff you should never have moved down here in the first place." He was sooo right!
All I can tell you is that, even though we thought we had done a pretty good job of getting rid of "stuff" before we moved, we didn't get rid of anywhere near enough.