My hats off to you! That is some story!

I would not do two roundtrips back to back, becuase:

1. It's inhumane, even in first class.
2. Any filight irregularity during the first roundtrip, then you have a problem with the second, since the "CONNECTIONS" are pretty tight.

Just out of curiosity, will the system let you check in on-line both outbound segments, i.e. lax -> bos? I think it's smart enough to not let you check in for the return?