Rolling luggage everywhere and trying to be cheap about everything (to the point of capsule hotels, lounge crashing or sleeping in airports) is probably somewhat contradictory or oxymoronic. I dare say I would drop the wheelies at left luggage or leave them checked and just do a light carry on bag if I was doing a quick overnight (or just use a carry on backpack). No point in lugging lots of stuff into town for but a few hours, right?