Htown, you described pretty much the way I pack my TriStar. I generally include my workout wear (1 pair shorts and several tops in the sleeve). I have several Tom Bihn packing cubes but really only use the small one for underwear and socks. Ended up buying Niike Free running shoes because they have thin soles and compress pretty flat if you put a couple of elastic bands around heel end of shoe. I have included a suit jacket in the sleeve but, I try to avoid this as it takes a lot of room and there is no easy way to fold it so it does not crease. You could possibly roll it and place in center compartment with work stuff on top of it.

This is the first bag I have owned that is totally aligned with the way I like to travel and I've not had to check it yet in over 200,000 miles of travel. Good luck with your travels.