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[Aldanga]

I haven't used my 360 for DVDs in a really long time (I've switched mostly to Blu-Ray), but I'm sure it supports subtitles with them. The player for all video files, including DVDs, is the same, which is why the subtitle option still appears. I haven't tested other subtitles with the 360, but it would be easy to test with a simple .avi encode. Testing for support for external subtitles would also be very simple.

I'm not sure that WMV supports subtitles. I cannot find anything online to suggest it does, but only people having problems adding subtitles to the container.

[Aldanga]

A quick Google search will return lots of results on codecs the 360 supports. I would just try DivX/Xvid or MPEG as they're supported with the media update.

I'm not sure about moving the subtitles with the other streams. You might want to ask some ffmpeg experts about that. Your problems could also stem from the type of subtitle, presuming containers are not compatible with every version.

[appliedcolors]

I think, you pc is not supporting your xbox. Upgrade your system and check it again.