Sloppy but Famous Contest

Drubin, I guess both I've mentioned players don't allocate too much time to brush or advance their music. Yayk!
Clapton isn't perfect, but very consistent organized and professional.

Some of my favorite artists compensate for lack of pure technical skill with feedback, distortion, and effects- Neil Young, the Edge, and Jack White. Of course, then there is Steve Morse who is a very gifted technically, but uses effects anyway because in the appropriate places, they sound cool. You don't want to take the soul out of the music.

Jazz and Blues are impromptu by nature. That defines true art to me.
The same song will be played slightly differently each night driven by momentary mood and feel with the rest of the band. I expect that.
Stepping out of one's comfort zone is the only way to grow.
Once in a while you hit a clam. life is alive!!! :)

Not sure what you're referencing re: Leo Kottke

I'm just a casual fan, but I saw him play in Minnesota maybe a decade ago. He clearly has ridiculous skills. (Or at least he did back then.) His genre tends toward the rhythm-centric, so he may play with pitch sometimes, but I don't recall hearing him blow it outright. I'm not saying it hasn't happened, I've just never caught it. IME, he is pretty much a metronome - I've seen few players who can keep time like Leo.

A related item, a piece of advice I once got from a guitar teacher: If you ever miss and play a blat during a solo, just play the same note again. Once is a miss, twice is quirky improvisation.

Many stages are open at times for anyone to take a crack at it:)