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Downsizing the house was a challenge but downsizing the Garage was HELL! The up side was my son took all my old stuff (tools, tool box and most other stuff) so I got to get NEW EVERYTHING! The new garage is actually quite large but I put the work bench across the entire front wall and would have a tough time getting a full size truck in. I also miss the driveway for washing the fleet but overall quite happy with the new digs. I'm fortunate that our vacation home near Tucson AZ also has a 3 car Garage (1 tandem stall) so I still have a bit of room for toys.
After 9 houses I would have a tough time with a "vintage" place. I just feel better about new technology and construction menthods. Good luck with the new place and post lots of pictures as you progress. I see you have a lot of old plates and might have a couple from Alberta Canada that I could donate to your collection. Send me a PM and we can discuss off line.
My wife and I live in SoCal. Will be relocating to the Central Coast of CA and a second home in the Central Valley. I have been looking for garage ideas, as we consider which vintage of home we want to purchase (and remodel/add onto). You've given me a lot of food for thought. Anything you would have done differently, in retrospect?