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If you want to use combo/team attacks, go find yourself an Item World stage with both Clone and Invincibility tiles. Combine the enemies into a single high-level melee-based unit, bring it down to minimal HP/SP, use the crystals to trap it on a Clone panel, and then prepare for the harvest.
Once you've brought your first weapon up to level 100 you'll be able to hand it to any characters you like and have them kill pretty much whatever you like, with no need to worry about using stronger characters to babysit them. You can get a high-ranked Legendary weapon to level easily by training up any units' Spear skill to 25, and then talking to the spear in the castle.
The "best and fastest" way to advance probably isn't very fun, but you simply need to capture strong monsters by bringing their HP and SP down to near-nil and then throwing them at your base panel. You can quickly get some lvl 9999 units this way, after which item levelling becomes easy, after which mass-character levelling becomes easy.
There's very little point in gathering large stacks of Gladiators. Creating enough separate stacks to fully slot out a strong item is worthwhile, since more stacks = better stats as an item levels, but boosting stack size does not improve item growth - and nor is it an efficient way to increase the power of your characters. If you're looking for specialists, go get Statisticians and Armsmasters instead.
Sadly most of the franchise kind of fails to pull you away from solo-leveling for optimization reasons. Disgaea 5 almost did it, kinda, except not really. I just ended up nuking everything with a Sage until I snowballed into oblivion.
Maybe Disgaea 6 will fix it? I like that the autobattle system kind of gives more reason to use squad tactics.
Anyways, other people have already laid out what I would know to do to help level other characters. Share the gear of your primary unit with others, do team attacks, etc. In Disgaea 2 and onwards you get Tower Attacks. In Disgaea 3 and onward Magichange which give you some more options to share experience. Disgaea 6 gives you way better options to share EXP and Mana, though I think they removed both Tower Attacks and Magichange.