Curtis,
I am a "road warrior" although the past 3 years it has not been as frequent. But for several years I had a minimum of 150 hotel nights.
You say your carry-on and suitcase are overweight. No one should be weighing your carry-on, just the checked baggage.
There have already been some good ideas posted. Here is my input.
If possible do not check baggage. The baggage apes will damage or lose your luggage. Normally they will find the luggage, but you will be without it when you need it. Don't use the rolling carry-on suitcases that barely meet the carry-on size requirements. They will not fit into an overhead on the small commuter planes. Depending upon the trip, I usually take a carry-on 'suitcase' or a TNF Rucksack. I always take my laptop bag, which goes under the seat, and sometimes I need to wear suits for corporate meetings, which means a separate suit for each day. On these trips I check luggage.
Reducing weight is just like backpacking. Is something multi-use? Some people wash clothes when traveling, I don't have the time or inclination. Take light weight underwear. Thin nylon dress socks weigh little and take up little space. Do you really need undershirts? Good, clean lightweight undershorts are a necessity. Extra storage items inside a bag are usually unnecessary, but I do use freezer bags for some stuff. Even if I check a bag, my toiletry kit is a baggie. I put dirty clothes into a mesh bag.
I don't use any cotton clothing items. Heavier and bulkier than alternatives. If you wear suits, quality light weight worsted wool suits are lighter, take up less space, and are more wrinkle free than most poly blends. And in the corporate world, the worsted wool looks better. I can wear a worsted wool suit on the plane, traveling from west coast to east coast, and it is not wrinkled when I land. One less item to put in the suitcase. Depending on the trip, I can get by with one or two sport coats and mix/match with pants. Again worsted wool pants and sport coats. I normally do not take much in the way of after-hour clothes. I just wear what I use during the day. Shoes can be bulky and heavy. Sometimes I need to bring more than one pair, and I use older Bostonian shoes with a narrow Italian styling, similar to wingtips. Light, always in style, and wear well. They are probably 15 years old and I have re-soled them twice.
On some trips I need to wear suits everyday, a different one each day too. On these trips I check a large suitcase. Never has it been over 50lbs, usually around 45 lbs for an entire week of everything, even some business material that goes inside.
Quality — When I first started traveling, I had to buy a new suitcase every year. The baggage apes are brutal. Tired of this, I went to a large luggage store that had an onsite repair facility because they repair luggage for the airlines. They suggested I buy Briggs & Riley. Lifetime unlimited warranty. After 10 years my checked suitcase was looking rather worn. A couple broken zipper pulls, piping on the corners worn, some of the inside lining coming apart. This particular model is no longer sold. I took it in (no receipt required), and Briggs & Riley completely restored it a no cost. The workmanship of the repairs was stellar.
I recently got a Briggs & Riley laptop bag, which is a 'clam shell.' You do not have to remove the computer for screening. Also in the corporate world, you don't want to show up at a client's meeting room with a backpack computer case — just the way it is. This laptop case looks good and has a lifetime warranty too. Just open it up and it goes through security. Here is a picture of my luggage. 4 items cover 100% of my trips. I take the laptop case (bottom left) and just one of the other 3. I have never needed to check the rucksack or small carry-on, and since I fly out of Palm Springs I always leave on a small commuter and connect somewhere else. Also, I often go on hikes or even overnight trips when traveling on business, and the rucksack does double duty. It packs into a very small package and I throw it into the large suitcase if I will do an overnight hike. I can carry my UL backpacking gear in the checked bag without going overweight. If I plan an overnight hike, I always bring the large suit case. For day hikes, I use the rucksack for carry-on luggage and as a day pack.
Good luck!!


TNF Flyweight Rucksack