will there ever be a category, Max NG+ All Bosses + DLC? I have a run that is sub 1:20:xx

Probably not, it's basically impossible to have a level playing field in NG+. Someone could get max level and the best chalice gems and have a significant advantage over everyone else. Not very conducive of a good competition.

If you start at a new file and have to get in every NG+ while time is running and there being a Offline and online category, because you need Playstation plus if you want to go to an chalice dungeon through a code, it could be interesting.

I'm all for this. My all bosses on max NG is also sub 120. I would say to level the playing field. The requirements are you must be max lvl 544. And beyond ng+6 in cycles.... Gems are completely optional but definitely necessary. And you can have a full inventory of items... everyone brings the best character they can make to the challenge of a max lvl speedrun. Weapons maxed best gems you have farmed. Whatever goes.