Honestly, if you're comfortable riding a motorcycle, you'll be fine in a Smart. I've driven most of my four Smarts across the country (at darn near Cannonball Run
speeds) and I think any generation will be just fine as a daily. No worse than my miniscule Honda Beat! I ran Smarts as my only
cars from 2012 to 2019.
If you get a gray market import 450 (1998 to 2007), be sure to keep the engine area clean. The alternators on them love to rust out and randomly seize. Clutch actuators can also be a bit of a pain as they can randomly stop working. Since these were never sold in the States, parts will come from Canada, UK, and EU and you may have to get creative with finding a mechanic.
If you get a 451 (2008 to 2015 for gas, up to 2016 for electric), know that the suspension can get a bit "crashy" and the transmission is a bit polarizing. You'll either be cool with it or hate it. These are pretty darn good at off-roading.
If you get a 453 (2015-2017 for gas, 2017+ for electric), these are pretty much the most "normal" of the crop. This generation was designed in part by Renault with up to 70% of the parts coming from the Renault end of the deal. These ones have turbos, the most modern features, and a suspension that's practically a cloud compared to the other generations. They're also very rare, but you can find them with a bonafide manual transmission!
Both the 451 and 453 have dwindling dealership support. This won't be too much of a problem if you have a good independent local mechanic or do your own work. I haven't been back to a dealership since my warranties ended.
If you do a lot of city driving, the 453 is going to be the worst of the bunch. The engine is tuned for around town and highway fuel economy. You'll be coming in and out of boost so much in the city that your fuel economy will be pretty abysmal.
A VFR is a sweet bike! I'm not sure we have too many motorcyclists here (I have too many of my own motorcycles lol) but it seems like a decent trade.