Is it common (possible?) for jumpseaters to check extra bags with the counter?

The reason I ask: At the end of next month I've got 5 days off, and I'm planning a short trip to Brazil. I'm an LGA-MKE commuter. To make the travel a little more effecient, I'd like to leave MKE on my last day and get right into Brazil. I don't think I can fit a 4-day trip's worth of clothes plus Brazil clothes in one rollaboard. I may be able to pull it off, but I'm not sure yet. I'd probably need a "Work Bag" and a "Brazil Bag."

I'd like to carry-on my Work Bag and check the Brazil Bag with the counter before I go to the gate at LGA on my way to work. I can leave the Brazil Bag in MKE while I work my trip, then on the last day swap it with the Work Bag and leave that one in MKE while I'm in Brazil.

I don't want to waste time by flying back to NY to switch bags.

Think anyone will give me a hard time about it?