I'm still waiting on 5 challenges.
I'm willing to challenge myself if it's OK with you, as I have more than enough tokens.
Thank you for your offer. Now that I checked out your Season 3 box score post, it seems you have all but 1 game already organized, so I guess you've received couple of challenges meanwhile (?).
We can make sure to add your HGL token usage for Season 4 though, if you're very eager to get rid of your tokens, so please don't worry... ;)
During Playoffs, it's sort of more encouraged to sending challenge even though you wouldn't be responsible for doing so (if one wants to try to speed up the match organizing process, with the cost of voluntarily losing one extra token permanently).
During Regular Season match organizing process, it's most of the time unnecessary, as we have more time to arrange everything (although of course there's also more to organize, and more to verify than in one Playoff round, and I seriously appreciate your attempts to get everything done well before deadline).
So at the moment I wouldn't consider that prohibited or anything (to send challenge yourself even if you wouldn't be responsible doing so), but the (only two?) downside(s) of you (or anyone who is not responsible of doing so) sending Regular Season challenges might be, that people could get confused if they receive challenges they shouldn't be receiving. Of course that challenge could be partly alleviated, if you'd send them BBMail to say you've sent them a challenge to speed up the challenging process, and/or to save them one token.
The other possible small downside would be, if it would be found that there has been a wrong court balance during Regular Season, and match result would have to be "erased"/penalties given due to that. Now if anyone would send challenges to each other, then it would be harder to determine who has had the responsibility to send a correct challenge in that RS match. (The responsibility question in this case is not 100% clear though, because match challenge receiver has also a responsibility to only accept correct challenges).