Who DOESN'T need tubeless?

Sounds like you have a set-up that's working for you. Not necessarily any need to change it.

I rode tubes longer than many for reasons similar to what you listed. Once I switched to tubeless tires, I did find I could run lower pressures without pinch-flatting, and this improved the grip of my tires as well as the overall ride quality.

Tire sealant is not infallible but it has saved me from small goathead-type punctures more than a few times.

Less rotating weight is a small advantage, too--although depending on what tires/casings you choose, this may not be very relevant.

With practice, the "extra hassle" of tubeless is very minimal. Changing tires is a little messier, but unless you are changing tires frequently it's hardly a big deal.

All that said, if it ain't broke, don't fix it, right? If you're having fun on a bike with tubes then don't worry about it. You mentioned that you're considering a bike upgrade. There's a good chance a newer bike will come with tubeless tires already installed. When that happens, you can try them for yourself--keeping in mind, of course, that tire tread, casing, size, etc. are also going to affect what you feel--and decide if it's worth it for you.

I occasionally put tubes back into previously tubeless tires at the request of customers when I was working as a shop mechanic. It's not super common, but to each their own.

If it works for you, don´t think of going tubeless as being some king of magical improvement. It´s not, it ads a lot of headaches if there is any king of issue that would be no problem at all with tubed setup, all for small benefit in terms of rolling resistance, lower pressures that are often touted as big benefit in reality are often out of window, because unless you run really burly tires you risk damaging the expensive tire instead of cheap innertube, or you will burp the tire oftenly, so if you ride anything even remotely rough and/or with a lot of high speed bermed corners you will end up using very similar pressures. So that leaves you with small difference of rolling resistance as the only realistic benefit for a lot of potential downsides. In my experience, in front wheel tubeless is mostly win situation, in the rear, the most reliable setup I had was tannus tube insert in light casing tire with tubolito to keep the weight very reasonable, it was close to exact opposite of tubeless strenghts and weaknesses, quite a lot of rolling resistance, but very stable, stiff feeling simmilar to DH casing tire with tube, just even more so. but at lighter overall weight than DH casing tire alone. If it wasn´t for me always wanting to experiment, I would be running it still, I wanted to give tubeless another chance in the rear, so I opted for DH casing variant of the same tire I was running with tannus previously and ARD insert. Overall weight is slightly higher, so far it works well and rolls faster. I will see how long it will remain trouble free. If it fails me again, at least I know what I will go back to.

great post, just_this_guy. instead of going long, i'll echo what anotherbikeguy said.

Maybe it's just me, but I can't stand the sloppy feel of the kind of low pressures that people ride with tubeless tires. Perhaps there is a bit more grip, but at the expense of feel and precision. I once got a free set of Mavic DMaxes and would just run tubes inside of the tubeless system so that If I pinch flatted the tube, the tubeless system would hold the air and get me down the mountain. I tended to ride about 32# front and 34# rear. Never lower. Maybe I'm just a freak though.

I went tubeless to reduce the number of flats I get.
I would commonly gets flats with tubes. On a typical ride, I would often pick up 5, 6, or 7 goat heads and I'd be lucky if they were in knobbies or not quite deep enough to puncture the tube. Sure enough, I'd suit up for a ride, or plan to take my bike to work for an after work session, only to find one (or both) tires flat in the garage. I got sick of it and finally moved over to tubeless for good. It was a hassle for a while, but no problems now that I have the right valves figured out.

If you're not having trouble with tubes, I wouldn't worry about it. I had constant problems with flatting inner tubes, but I still had problems with flats and dented rims after switching to tubeless. It took me a long time (and the invention of tire inserts) to get to a truly happy place with tubeless. It sounds like you don't have the same problems, so if it ain't broke... don't fix it.