While I realize that for many users the chat is not a big part of the community but its really what keeps me engaged with the site and I think it would help keep other people (as in new users) here as well. Would it make sense to implement a feature where you can gift a user the gap amount of reputation needed to chat? Gifting would involve the gifting user permanently giving enough of their own reputation to the user they would like to join chat. To lessen the blow, perhaps the receiving user needs to accept the gift of reputation and join the chat so that reputation doesn't just disappear (this isn't a requirement but I think it would make people more willing to use the feature as there would be less risk involved). It could also be a privilege that is unlocked at a certain reputation level.
When would this get used? Sometimes there are bad questions for the site that would be enjoyable to discuss with the person looking for information and beneficial just to share opinions and experiences on the topic in real time. Often times, though, the user doesn't have enough rep to chat. If we had the ability to gift reputation to get people in the chat room it would lessen the blow of their (usually first) question being closed to oblivion, get them involved in the community in other ways, and hopefully become active members on the site.
Why would this be a good idea? When I get the feeling of "boy I wish I could chat with this person" it is because the question they asked is actually on a topic that interests me as a game developer meaning its generally not your basic "how do I X" or "Why doesn't this work" questions which means this person actually has the potential of contributing useful content to the site even though their first question may have been bad. We want to keep these people around so instead of completely putting them off of the site altogether by closing and downvoting their questions, lets get them in chat and have valuable discussion on the topic they wanted to find out about and help them get their next question right.
I personally have not given this idea full thought but there are definitely times I wish I could say "Hey! Join us in chat and lets discuss it further!" but I can't. Sure they could easily get the 20 rep needed to join chat but then the onus is on them and odds are I'll never seem them again anyway. It would be nice to have the power to be proactive in encouraging people to get involved instead of waiting around for them to get motivated on their own.
Needless to say I thought of this as a "simple" solution and wanted to see what the community thinks. If it doesn't make sense for the StackExchange network and let me know why. I'll probably see things your way.