Starting this thread to collect lessons learned. I could post elsewhere, but Bicycle Mechanics is too down to earth and the "41" too immature.
Lesson Learned #1 (my first lesson) - when you have the bike on a stand and find a wire embedded in the tire, don't pull the wire out when it's in the 12 o'clock position. All the air leaks out and when you rotate to the 6 o'clock position at the resulting low pressure all the latex runs out. The good news is that I had apparently ridden the bike back home with embedded wire without loosing pressure.
(Note: 12 o'clock is what we call "up" and 6 o'clock is what we call "down". The analog representation of time is going the way of the Dodo. )
Cannondale SuperX, Santa Cruz Tallboy, Surly Krampus
Not doing it yet on my roadie. So no experience here. But between my son, wife and myself I manage 6 MTB's with various degrees of tubeless legitimacy.
Lessons: Stan's sealant need to present. Stan's sealant dry up in under 2 months in the desert southwest. Stan' sealant dry up just as fast in unused wheels. In other words, tubeless will provide the best returns if the bike is in as much use as possible.
And it's difficult to assess the fluid levels.
Any combo of rims and tires can be a workable tubeless setup, either using split tubes, all sorts of tape or other paraphenalia. What determines the degree of success more than anything is tire pressure, or rather willingness to forego the lower pressures.
If you're a DIY'er a compressor is more than a little handy. Not essential, but....
My LBS did suggest in the warm months adding 1 oz of Stans per month; I stretched it to every too much just due to laziness. In the summer I lost less than 5 psi/day (85/90 front/rear pressure). This winter I finding a negligible pressure drop. At my 195 lbs this is a lower pressure than I was running with tubes and the ride is appreciably better. Tires are Hutchinson 28mm Sector (or Secteur).
I suppose once or twice/year one ought to dump the old stuff out and inspect the inside of the tire. That's something I'll have to look into.
I'm running a regular Velocity A23 rim with two layers of Stans rim tape.
Just to circle back to my incident with the wire: I rode the bike with that embedded wire and it subsequently lost no pressure over night. If I had been doing a descent with a tube/tire combination a wire like that in the front tire could have been disastrous. I haven't experience a front flat on a descent and didn't switch to tubeless tires to mitigate this sort of risk, but every little bit helps.