Hi Chris.
I didn't do that anytime, but I have some ideas.
First, your drummer must record the drum - it's the first thing, because all other musicians must follow the drum beat tempo (timing)...
After that, with the drum ready, everyone can play and record alone (listening to the drum beat in a phone).
I suggest the following order after drums: bass, tyros 5, guitar and finally vocals (if have).
For better quality, I prefer to use WAV (is bigger, but clean) - you can also convert to high quality MP3 (more then 256).
After that, you need a software like Apple iMovie, Adobe Premiere and so on to mix everything...
It's what I would try .... Timing (tempo) is the most important question here.
Regards,
Pedro Eleuterio
Brazil