You got me because I've actually been pretty lucky with tubes. But I like tubeless on my modern bike because of the comfort and because no tubes = no snake bites. On small 26" wheels I find that just 1/4 a bar makes a huge difference in comfort and control. If I can run a little bit less pressure and also not worry about pinch flats when doing it then I will be happier. Even if I have to run the same exact pressures I will feel better knowing there's no tube to pinch.
If you don't have to worry about punctures from thorns, etc. and are only concerned about pinch flats, tubeless is worse/more expensive because snake bites still can happen, except now the holes end up in more expensive/ less repairable (even with a patch, structural casing strands are broken) tire casing. In a pinch flat with tubes, the tubes have a protective effect for the tire casing.
On the wheels and tires subforum currently, someone was asking a kind of related question about fattest tire size for his vintage 26" rim and bike. I pointed out that his rim was probably around 17.5mm internal width. When I switched to 2.2" Race Kings on my 17.5mm internal width rims, I got what I wanted in ride quality. But I'm still restricted by how low I can go in pressure because the tire will squirm/collapse below low 20s psi in high G turns (at my weight of about 155lbs). So you can't do the 16-17 psi thing that other people can do with wider internal width rims and 2.4 tires.
I went through this thought process a few years ago because I like my old '90s bike (that I have ridden from new and will never get rid of) and have optimized (if not a complete retromod) it to the extent that it can be reasonably optimized. In the end, I decided that tubeless didn't make sense with the old rims. I didn't want to deal with the hassle of using split tube or screwing around with how many layers of tape for no real gain, since I don't get punctures where I live. My last flat was years ago, and I didn't even really mind getting it. Also I ride seasonally (ski in the winter), and didn't want to mess with refreshing sealant when I have no maintenance now other than pumping up the tires.
I've considered getting wider 26" rims at some point but will wait until the brake track wears through my front rim before changing it up. There are 26" rims that are 25mm internal like the Velocity Cliffhanger, but it's probably 160+g more just for one rim more that what's on the bike now. The Sun Sta-Tru TR25s are 25mm internal, and intermediate in weight between the old and the Cliffhanger (still 505g vs. ~440g with actual weight lower due to rim wear) but I see no reviews of that rim. There are 26" carbon rims that were tempting, and I did a lot of research on rim brake and carbon rims/carbon rim brake pads since I run rim brakes. But even with brake pads for carbon rims, they would be a downgrade in braking capability (my current rim brake setup is really good). 25mm internal width might allow lower pressure than the low- to mid-20s psi that I run now, but I'm actually quite happy in every way with 2.2s on the narrow rims. . . great upgrade to the original 1.95s or previous 2.1s.
In the end, the best compromise for me (at least until my rims wear out) for my type of riding is to keep running tubes on 2.2 tires. I use the lightest 2.2 tires (Race King Race Sport sub-480g) and butyl tubes (Conti superlight, sub 100g) that I could get.