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TRIM definitely works in Windows 7 on TrueCrypted SSDs. The TrueCrypt documentation explicitly states it doesn't block TRIM on devices within the scope of system encryption.
No, it won't kill the drive faster. The initial system encryption will of course write to every sector, but that's a one time thing, so maybe a tiny bit faster. The issues with SSDs are data leakage due to wear leveling, which you can avoid if you encrypt before storing any sensitive information, and TRIM causing free areas to be all zeroes, which lets a person distinguish used from unused areas, which I don't really care about. The TrueCrypt site has articles on both these things.
TRIM definitely works in Windows 7 on TrueCrypted SSDs. The TrueCrypt documentation explicitly states it doesn't block TRIM on devices within the scope of system encryption. When I look at the encrypted system partitions on my two SSDs (Samsung 830 and Intel X25-M) outside of Windows and unmounted in TrueCrypt, I find a ton of zeroed sectors, and my image backups of these unmounted partitions reflect this in their compression statistics. (The imaging software can't see the file system, so it has to back up every last sector.) Both drives have but a single partition, and one of the drives is formatted to capacity. The zeroed sectors have to be due to TRIM.