Yeah, we played the one car game for a little while, it's pretty nice. We honestly rarely use the wife's car and even less so now. I kind of like the simplicity of the GTI and don't really miss having a more expensive car. I think I'll likely get a Mk8 R just to have one more go at a manual new car before that becomes tricky. But I have been giving more thought to a third car as more of a play thing, especially as the R would anchor the kid hauler role pretty well. I work 200 miles from home, but only have to do that drive once a month or so, but that does make a Caterham or similar a little impractical for that role, but it would be ideal for local roads.
Funny, just noticed you're in Chicago. We nearly moved up there a few months ago for the wife's work. We would have been right back in the single car discussion if we'd done that.
My R is on storage insurance. Hasn't been driven since November. I didn't want to buy a dedicated winter set and wont drive on summers below freezing. Got it in April and it only has 5,000 miles on it, w half of that being me driving it home from Baltimore where I bought it and a round trip visit to Kansas City.
We live 100 yards from the subway stop I take to work and its only like 20 minutes to my office if we ever go back so we could get away with 0 cars without an issue. I moved here from Austin in 2015. Made the drive straight through in my mk6 GTI. Kinda did my single mid 20's thing in Austin for a few years. Good times. Miss the coeds, brisket and the weather (current issues not withstanding).