It depends how the bagless is implemented. I have a small bagless corded vac that is rather messy to deal with, but my parents' upright bagless packs everything into a measuring-cup-sized canister that dumps very easily.
My problem is cleaning the filter. So you have managed to dump the cup without getting dist everywhere (I used to do it outside due to the mess). Now you have this pleated filter that is all plugged up with dust bunnies and other debris. I have never managed to get one reasonable clean while staying reasonably clean.
