Assuming status quo, I don’t see an issue late season for gear, most guilds I know of are either extending or on break at that point anyhow. I do agree it should not be beyond their kill level in a regular season.
The reroll tokens would be awesome but Blizz has said no repeatedly. That said rerolls were pretty deterministic too, you just had to fail two rolls and hold the roll for the boss you needed.
Good to see a different perspective, for me it’s a lot to do with the shorter seasons I think, everything on my character will be gone inside of 6 months, it’s just a tool to achieve boss kills and do keys. Whatever I have including the legendry axe will be chucked into the void as soon as TWW goes live, and that gear will be gone 6-7 months later after that.
That again goes to Zoumz’s post, gear doesn’t show our progress anymore. Gear is transactional and the achievements are what lasts on your character. Think the best answer they had were the artifact weapons, however their early implementation wasn’t great.