Honestly, if you're checking it, what's the difference (I only find these things to be a hassle if you need to carry them around in the airport. That only happens if you have limited checked baggage allowance. Something that never happens to Dan)
You need to get all that stuff in the car, to the airport, check what you need. Then collect everything at the destination, get it to the rental/cab, to hotel. Oh yeah, and then there's the little kids (not a good idea to lose those) that your wife is watching so she can't help you shelp all that stuff. Then do it all over again when it's time to leave.
#PITA