Yea I was kinda someone in that middle ground. The Werbeski’s are 72mm wheels on an aggressive skate. I played hockey so I didn’t really gel all that well with super small wheels, I needed more power and speed.
I feel you bro, Jet Set Radio and Dreamcast were a huge influence on me personally as a kid. I literally tried to live the Jet set radio life in high school, aggressive inline and graffiti at night.
You’re 100% correct. They’re still a pain in the ■■■■■■ carry around, and put on/take off, the design had a lot of flaws for sure. I always wanted a Soap shoe that “clicked” into a baseplate eliminating the need for all the straps and stuff up top. Basically like the freeskate, but it had some sort of “locking mechanism” to keep your foot attached to the baseplate, then you could click a button and unlock your shoe and go soap around.
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Talk to me about comfort and learning curve at your leisure
The extent of my knowledge is seeing it on someone at the mall, and thinking, wow, that looks awesome.
Could you walk in these around town and they feel perfectly comfortable all day?
These are probably not considered comfortable by most. I wear Xero shoes and they are really thin soles. Some people also wouldn’t consider those comfortable either. The problem with Heelys is the way it makes you walk; almost on your toes. However, the shoes are fun! I came from roller blading prior to Heelys. I could skate before I was potty trained. So my learning curve was a few minutes or an hour. When you figure it out they are fun! If you really want to take it to a whole new level; learn to Heely while yo-yoing 
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Wish I’d see them in my size. I’ve rollerbladed for decades. Still do once or twice a year. I’d buy heely’s in a second.
Used to own a pair of SOAP shoes in highschool and owned a pair of Salomon grindshoes in my twenties. I’ve looked around for Soaps…but can’t find them anywhere anymore where I live.
Just for fun. Here’s some video of me and my friends in the late 90’s.
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There are some on EBay.