I've got another gaming confession you won't like

[Vitiman]

Sonic 1 is dated as hell and kind of ass

See, this is an opinion I see a lot of and I can't say I've ever jived with. Certainly, Sonic 1 is a different feeling game from its successors, but how does that make it dated? The first Super Mario Bros. also lacks many common conventions of future Mario games but that game is still relatively highly regarded.

If anything, I would expect someone who is more of a traditional platforming fan such as yourself (going off of your praise of SMW and the DKC trilogy) to be more at home with the original Sonic, which is much more platforming-oriented than any of its sequels ever were. Or perhaps the 8-bit Sonic games would be more up your alley.

Then again, I suppose if your main beef is the design of the character, I can't say I know how exactly to fix that. There are a million and one mods of the Sonic games that let you play as other characters, maybe you could look into those?