Yea, packing for biz travel is a real art form, and overpacking is probably the biggest problem. I always packed things that would be really flat and coordinated well together...usually black or gray as a base, and then shells and shirts of different colors. The Foxcroft Wrinkle-Free shirts are great for travel. I did my 'ironing' by hanging clothes in the bathroom and running the shower really hot...works great! Kept my shoes to 2 pairs...one I wore on the plane, and they were slip-ons for easy on/off at security and running for flights. I dress pretty simply anyway, so this wasn't a big problem for me...minimal jewelry, accessories, etc.

I also invested in Briggs & Riley luggage...a carry-on and a wheely bag. The carry-on went overhead and the wheely under my seat. I didn't carry a separate purse. Expensive, but best luggage on the market with a lifetime warranty...even if the airlines does the damage! I used to never check bags unless the plane was a pond hopper, but when they restricted the liquids, gels, etc. it was easier to check my carry-on and keep all that stuff in it. (Since there were occasions when I would get stuck for 10-14 days, I couldn't count on the 3oz rule, but you might not have a problem with this.) I only 'lost' my bag once and got it back the next day.

When you go to Maryland and change planes in Dallas, are both flights on the same airlines? If so, usually they will put a special TRANSITION tag on your bag so you don't have to pick it up and re-check it. I doubt you'd be able to make it in 30 minutes if they don't given security and racing to gates. Make sure to ask them about it.

I'm job-hunting now, so...no...I'm not doing the same thing. I wouldn't mind the travel that you are doing, but no way would I work a job where I flew from coast to coast, stopping in 4 different states in 6 days!!!