I’ve had a Chrome bag for 15+ years now. I’ve been very impressed with the durability and with just how versatile it is. I use it for everything.
I've got a Saddleback briefcase if I need to look fancy or I'm not carrying it too much, yeah it's annoyingly heavy but gorgeous. Ogio backpack for trips where I don't need to carry much and for the second laptop when I take it. Got this roller from Amazon - https://smile.amazon.com/gp/product/B083GH3L2N/ref=ppx_yo_dt_b_search_asin_title?ie=UTF8&psc=1 when I got tired of a sweaty back in airports. Also has enough room for a spare set of clothes if I do a super short trip or I can combine it and the backpack. Upside for normal races is it also hauls my radios and assorted cabling for the scoring stuff. Important thing for me over the years is a luggage strap so I can stack things easily rolling through airports/rental car joints/whatever.
The one you bought 15 years ago is head and shoulders better than anything they make today. The quality of everything they make has gone down the pooper for at least the past ten years or so. I've got one that has crossed the world a few times at this point, and apart from the velcro flap not sticking anymore, its been very good as a carry on computer bag.
Briggs & Riley...lifetime warranty. https://www.briggs-riley.com They have a distributor in New Berlin, WI if that's close.
Then this is what you want. I keep my full size 9mm in the pocket and it works great. I am a realtor an its nice it have it in there.
I had a nice custom leather messenger style bag made by Go Forth Goods and couldn't be happier. I had to get an oversized custom bag made since I use 17+" laptops and I wanted something that didn't appear as though I borrowed it from my kids. I've had it for 5 years now and it's still as nice today as ever. The leather ages naturally and I get complimented on it regularly...which I've always considered odd since it's just a computer bag. I use it often since I find myself on the road at a minimum of once a month for a few days. This is the specific model I had them modify to my measurements: Harris Briefcase
I have the Duluth Trading one. I have had it for about 10 years and it still looks great. It has plenty of room for the laptop, cords, writing stuff and a 1911, with no problems. Flying the regional carriers in AK doesn't require going through security, so it was nice when going to town.