Akikan!: The chance of character songs seems unlikely, as the show is going the Go-onger route in numerous ending theme remixes. Much like the last time Nomiko did something like this (Magical Pokaan), the variance in endings often makes them come close to character songs as it is.
Minami-ke Okaeri: Already got a character song album with "Shunkashuutoujo!", so that's nicely covered.
Maria†Holic: Shaft shows stand a really good chance at getting character songs, and there's a well-established voice cast here too. While nothing has been formally announced yet, I wouldn't rule it out entirely.
Sora wo Kakeru Shoujo: This one is a definite "yes"! Three character song singles for Leopard's leading ladies - Akiha, Honoka and Itsuki - have already been confirmed by Lantis. This is just for the first half of the show, so the odds are there may be more. You can expect a news report from me when that time comes.
Asu no Yoichi!: Another one that's confirmed. Four singles, one for each of the Ikaruga sisters, have been confirmed. I certainly wouldn't mind if there was more (namely, character songs for Tsubasa and Angela), but even those four should provide a nice set of tunes.
Chrome Shelled Regios: There will be covers of the ED featuring the girls, but I'd place the chance of songs to be in the same middle ground of "I really have no information either way". However, for some shows from seasons past, I do have information, which takes us to the next section...
Past Shows, Future Songs
Toradora! Update: A character song album has been confirmed for release. Songs for at least Taiga, Minori and Ami are certain, but there's quite a lot of characters to work with. Looking forward to a tracklist for this one.
Kemeko Deluxe! Update: The Limited Edition DVDs appear to include remixes of the OP and ED, but there will be character songs. A series of "Deluxe CDs" has been confirmed for release, the first of which will feature a song by M.M. and a duet by Fumiko and Aoi-san. What the others will hold is something to look forward to.
Strike Witches Update: A series of five character albums was recently announced, covering the complete 501st. In order:
- Yoshika and Mio
- Sanya and Eila
- Gertrude, Hartmann and Mina
- Lynette, Perinne and Yoshika (again)
- Charlotte and Francesca
Given the complete and utter success Strike Witches was, I'm glad to see these appearing.
Kanokon: What's this doing here? One thing gives me reason - 5pb.'s Kanokon Complete Song Collection (titled "Nice Body") will be released, and, besides all the character songs that were included with the DVD releases, there will be two new ones on there. The songs are by Haku (Sakakibara Yui) and Ten (Kitamura Eri), original characters made for the Kanokon SE game.
Kannagi Update: The fifth DVD will include all the songs sung in "Karaoke Senshi Mic Takako", which, given the character's personalities, fits them pretty nicely. Confirmed and ready.
Looking forward to everything on this list in the future, and the news of what will be.
Keep your eyes and ears open.