So today I decided to give the two bag thing a shot and it worked out great for me! I've got my LV Neverful MM with my coach 6x8 agenda, a notebook, a book to read IF I get a break, a few snacks, pleated ergo wristlet with pens and other little work related papers/items and a file for a report I'm working on. I also brought my Legacy Shoulder bag in teal leather that I've got my wallet, personal 3x5 coach agenda, LV pochette with misc electronic items and my HS small cosmetic case with some lipglosses and other makeup. I love how all my stuff is nicely organized and I can find whatever I'm looking for. I did try out the HS tote instead of the neverfull and I don't think that looked too bad either. Thanks everyone for your help 
