Hi, I am hoping the wise folks on this forum can assist me in choosing a bag configuration. I think I want a dedicated laptop bag and a backpack-capable travel bag, but I'm not 100% sure. The choices probably should be straightforward, but I'm in full-on analysis paralysis, having spent days reading internet reviews, etc.
I typically travel ~5 times per year for my job. This includes 1-2 international trips, usually to SE Asia. My typical trip duration is 5-7 days. When I'm not traveling, I carry a mid-size laptop (Dell E6410) and associated charger, etc. Generally, I don't have a need to carry much besides my laptop/charger and a few other small items on a daily basis.
Currently, I use a large Timbuk2 laptop backpack as my daily laptop bag. When traveling, I carry the Timbuk2 backpack (placed under the seat) and a Tumi roller. I'd like to replace the backpack with a dedicated laptop bag (briefcase style preferred), and I'd like to ditch the Tumi (and rolling luggage in general) in favor of a backpack-capable travel bag.
When traveling, I like to avoid the anxiety of trying to find overhead bin space, so I prefer a bag configuration where the larger clothing bag is most likely to fit in the overhead bin. Currently, I will often check a bag for a more stress-free experience, but I'd like to stop checking bags and only carry-on. To reduce what I need to carry, I'm planning to bring fewer items, do laundry once or twice on a trip, etc.
Any advice on what bags I should be looking at? As I mention above, I think a dedicated laptop bag and a dedicated travel bag would best serve my needs, but I am open to suggestions. Also, if there is more information I can provide to help guide your advise, please let me know.