I’m fortunate that my bike came equipped with the capability out of the box, so I’d just need to buy the valves and fluid to put in there (the wheels are already taped even).
But it came with tubes installed, and I have just been super lazy. But now I’m really considering making the switch.
I've used tubeless since my first adult bike and I'll never go back. I loaned out my bike as a courtesy car bike while converting one to electric but I got tube flats 3 times on it in the short time I've had this one.
Between three bikes, two e-scooters, and probably 20,000km of riding (in four years) on everything from isolated trails to shoulders littered with every type of debris you can imagine, I've only had two flats:
The first was on my escooter, and it happened right in front of my home (puncture). This was when the tire was due to be replaced anyway, so there may simply not been much rubber left.
The second (a bike) was likely caused by a poor inner tube installation when the tires were replaced.
On my bikes, I've currently got three very different types of tires:
Schwalbe Marathon 365 GT. Heavy, all-season, robust, and "puncture resistant".
Schwalbe Big Apple. Medium puncture resistance, smoother treads, "balloon tires" (not fat tires).
Continental Ultra Sport III. No built-in puncture resistance. Slick tires. Very inexpensive.
I check my tires for fragments, cuts, etc. They all look clean. Like, nothing but regular wear.
The Ultra Sport tires in particular have seen 2000km in three months, and they are pristine.
Is it just luck? I don't know, but it ways interests me when someone says they get multiple flats on a regular basis.
In my case the problem is that part of my local trail butts up against a golf course, and when they mow they just blow all the clippings onto the cycling track. We have a lot of goat head stickers here so you end up riding through grass with these little landmines in them.
All the flats have been from little thorns from the stickers.
Do you have the option or desire to use Schwalbe marathon plus tires? They should offer excellent puncture protection, but they are heavy.
Tubeless won't actually prevent punctures, so depending on your needs and ride style, I'd consider better tires.
The tire rolling resistance site has tests that compare puncture resistance (and other specs) among just about every major tire out there, so that could be a starting point.