Not a Jazz superfan, but I do love guitarists who can play. Joe Pass was a titan. Absolute master of the instument

[ProfessorGAC]

4. Yes

The Polytone sound. They're out of business now, but there are so many out there, we'll be hearing that sound for a while. CI always felt that sound really did an injustice to guitar.
Django's guitar always sounded like a guitar to me. You can hear the "ping" of the string on attack. So, I've always been good with him. Cool stuff, good sounding. I wonder how he & Grapelli would have sounded with modern recording methods.
That tone kept me from enjoying jazz guitar as much as I otherwise would have. There have been some sax cats whose tone I found off-putting, but not many.
And, most my jazz listening was piano focused, which was fine by me.