Thanks for all the tips!

Rolling computer bag plus duffel might be the best combo. Will read through the stickies and see what pops up. That also might be the cheapest combo, too. I like that

I'll check out the eBags TLS. I have the newer Mother Lode 24/25" rolling duffel and love it - can pack a ton into it, although shoes still trip me up. It looks really beat up after two trips to Asia, but still works fine. I also use Osprey packs for backpacking so love those, too.

Two laptops is an unfortunate must. I'm trying to get away from three. For work I need two machines to do my product demo, and we usually take a third as a backup device.

Unfortunately the reason I think I have to go without checking a bag is a connection of just over one hour in Panama City going each way between business and wedding. I need the suit with me for the wedding. On the return if I miss the connection due to bag issues I miss my meeting and I can't have that happen. I'm trying to find flight combinations that work to allow for reasonable success in checking a bag, but not sure that will happen. Otherwise I agree 110% - this is the absolute reason to check a bag: long trip, lots of various stuff, etc. I don't even need the bag for business, I can carry enough things on to survive just with my computers and a change of clothes (or buy at the destination). If I can get connections that work with at least a day or two in between to allow a missed bag to show up (or replacements to be bought) then I'll be checking my way around.