Keeping the show as a WAV file would eliminate the timing problem, but the resulting audio files would be huge. You could keep the SSTV as a separate audio file in WAV format, and send the program audio as an mp3 or WMA or whatever, but that might be a hassle for your relay operator?
Also, for whatever reason, I have noticed that SSTV images, when transmitted in AM mode, often looked "washed out". I'm not sure if this is due to the transmitting or receiving side (or both). IIRC I've sometimes demodulated them in SSB mode, resulting in a slightly better image.