everything but the kitchen sink
Are you an "everything but the kitchen sink" kind of packer? I used to be. Not anymore. Not even a little bit!
Years and years of schlepping my own bags have helped me override my natural tendency. It is considerably easier to travel with just one bag (or a bag and a backpack, for longer trips). And since I travel fairly often, I'm pretty good at guessing what I'll need, as long as the weather forecasts stay accurate.
(The second time we went to Chicago, it was much colder than predicted. I almost had to buy a sweater. But I managed. Mostly because my MIL generously let me use the washer/dryer in her hotel suite.)
On the other hand, schlepping the car seat/ booster seat is still challenging for me. We have a rolling bag (which was perfect when I had to schlep the OMG HUGE car seat through airports) , but it seems like overkill to use it for a booster seat. I'm going to see if I can find a bungee cord and jerry-rig it to my rolling suitcase, since I have to get it to/ through Penn Station by myself and still be able to hold Remy's hand.
I have a feeling that it will all work out. I did manage to get my two year old, his car seat, a stroller, a rolling bag and a backpack to Europe by myself, with a six hour layover (the stroller came in handy as a push cart and was a necessary thing for naps). If I can manage that, I can manage anything!