it sound like it's nothing you can't handle, you'll definitely managed the commute miles, however I feel that the messenger bag probably will bother you after a few weeks.
If it's a good bag and has enough adjustable straps then it shouldn't be a problem, I can cycle indefinitely wearing my PAC, I feel weird when I ride without it in fact.
If it's a good bag and has enough adjustable straps then it shouldn't be a problem, I can cycle indefinitely wearing my PAC, I feel weird when I ride without it in fact.