How can you enter city to bribe the authority, if you are Vilified and they are shooting on sight?
Ok, Donating caps to an ambassador of a community/town. There will be one of each in every single town so if your Vilified in Lets say VC you can easily go to NCR and pay the ambassador there and get some rep back.
against, you know that you gonna lose reputation by doing evil deeds, so be ready to pay for them. (not in caps)
Just wait for more quests, quests increasing reputation, quests can't be abused only by one kind of players, everyone can do that, regardless of rich/poor, powerbuild/crafter, etc.
Against. Another feature to help rich griefers ? We don't need it.