Having a good amount of reasonably well maintained dedicated bike lanes would have made rollerblading to work a lot easier!
People get creamed on bikes all the time in bike lanes. Pedestrians on the sidewalks and bike paths just don't pay attention to anything other than what is 3-4 feet from them, and are always forcing you to dodge if you have any kind of speed if you're just even jogging.
It's more a cultural problem than a city planning problem. Contrast how seriously bike lanes are treated in (say) Munich, which is very seriously.
I am seeing more and more e-bikes though, which, since you can keep up with traffic relatively well, allow you ride in the car lane under most circumstances. That's what I do, and if some dickhead really feels the need to pass me when I'm going >25mph, I'll give them a wave at the next light. And probably be shot in the chest one of these days.
I used to skateboard from a lot by the Metra station to the office @ State and Madison.
Most fellow commuters I encountered were visibly bothered by sharing the walkways with someone adult-sized traveling 2-3X their speed. I'd expect a similar level of antisocial friction with these shoes.
Though it has been well over a decade since I did that, maybe people have since warmed up to sharing sidewalks with ebikes/scooters by now.
The best thing you could do with an escooter is to do what bike riders do to be safe, which is to take the entire lane. Car's might get pissed and honk when they pass you, but its better to force them to merge into a separate lane to get around you, than to try to squeeze through the same lane you are in and force you into parked cars or the gutter.
Basically I don't think there is any safe and responsible way to use an e-scooter. I don't think they should exist, it's just a bad idea. e-bikes are great though.
That said, when I lived in Chicago, I used to see a lady who rollerbladed to the office. I am sure you're thinking, "Young techie, jeans & t-shirt", but you'd be wrong. 40's or late 30's, dressed like an exec. Wearing a dress, make-up, string of pearls, with a fancy handbag, nice haircut. I don't think this is a relevant data point (clearly an outlier), I just thought it was awesome and wanted to share.