1. I'm a huge tubeless fan, but, no, probably not worth it if you're only using them a few times per year.
2. Yes.
3. Yes, always carry a tube unless it's the kind of race where you're done if you flat, and you have an easy way back to the start.

PROS
- no tubes!
- less flats

CONS
- some tire/rim combos are hard to seat
- tire/rim combination can make it IMPOSSIBLE to reseat tire while on the side of the road.
- sealant needs to be changed every six months or removed in the winter if your bike sits like mine.
- need to carry/use tire plugs for big punctures
- tires cost more
- if you need to change tires frequently it's a pain in the ass
- need to use the tires frequently or the sealant dries out.


I rode some pretty gnarly terrain with my tubeless that may not have been rideable without a pinch flat tube.
However, I flatted twice with tubeless where it didn't seal and could NOT reseat the tire on the side of the road. My jersey and hands covered in sealant was an awful mess.
I have since gone back to latex tubes for the road riding. Anything 28C or less is not worth it in my opinion.
For gravel I put on the tires in the spring with fresh sealant, and remove them in the fall when the snow flies.
Big tires are easy to mount and remove. Narrow tires are not.

One/two more question(s)....

I've read that sometimes the sealant fills the hole and you can finish a ride/race.

Is that true? Could a co2 get me up and running again if that happens?

Does it depend on the size of the puncture?

Do I need to replace the tire after a puncture (assume puncture size dependent)

(despite the answer being yes to a sealant fill, i'd still have a tube)

Generally the sealant will seal the hole before much air escapes so no need to stop and add more from a co2. If the hole is too large and you need to patch it, this is what I carry..
https://www.amazon.com/...1693889013&psc=1
Why wouldn't you ride the HED wheels all the time?

Yes, and yes. On the second yes, that's not all cases, but "very often."



Yes. Some punctures are unseal-able. Or only seal at very low pressure.



Rarely. When there's a big gash that can't be repair by patching the inside of the tire. Or some types of sidewall slashes. Approximately the same sort of punctures that would result in trashing a normal tubed tire.

Excellent. Thanks!

I would likely ride them more than I said especially after having them for sometime.

Likely being over cautious and I suppose riding them less to keep them in good shape saving from the beat up of lots of training miles.

That alone makes it not worth your time and effort. Also consider that you have to still carry a tube and CO2 because it won't seal every time.

Add in the fact that changing to a tube after you have used sealant is a sticky and time consuming effort (no something I would want to do in a race) and I wouldn't consider it.

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"...the street finds its own uses for things"

How often are you flatting now? If it's not a lot, it doesn't seem worth it. (this is coming from someone who rides tubes)

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Strava

most have done a good job of answering your questions but i would add a couple things.

i would recommend either the Conti 5K or the Scwhalbe Pro 1s. i ride the 5K but both are very durable and low rolling resistance. i was on the Corsi Speed and while they were fast, it was a pain to get on and off the rims. it you have to add a tube while on the road you might be SOL. and also, they are way more "delicate". every puncture i've had with the 5Ks has sealed up while riding. lost some air but always rideable. i carry that plug kit just in case and of course a spare tube. you can always add air if needed.

Why wouldn't you just use Continental GP5000 clincher tires with latex tubes?

Yes, race use only seems to be crying out for clinchers + latex.

i was/am leaning towards just staying with clinchers, but many people really seem to like the tubeless, so i was curious.

i'm not even sure there what the real benefits of using tubeless are over clinchers. other than maybe finishing a ride without having to switch out a tube. comfort, rolling resistance, speed?

part of my reason for not using race wheels in training is that my regular riding roads are notorious for causing flats, especially on racing tires.
we all use thick tires for training which helps a lot, but is not a guarantee.
no one that i ride with is/has been willing to switch from the comfort/knowledge of clinchers.

there seem to be a lot of people who really like the tubeless and dont often get total blowout when riding them.
however, the consensus seems to be it sucks REAL bad when that happens, but maybe doesn't happen a lot.

i am a little hesitant to use a racing tire on these roads but was thinking about trying and if i got a total blowout and didnt want the hassle of dealing with the sealant and trying to get a tube in, i am never all that far from home and could easily be picked up by my loving supportive albeit sometimes annoyed spouse.

Latex Tubes and 25c Michelin Power Competition tires on 19mm internal rim beds. I ride a mix of urban, suburban, and country roads. One flat in 3000 miles, and it was nasty enough to waste pretty much any type of tire.

All I can say is I have ridden some fast wheel and tyre combos but after my first ride on GP5000 TL’s I was hooked and will eventually convert every set of wheel over regardless difficulties. The ride quality to me just feels next level and is obviously fast.

GP5000 clinchers with latex tubes are just as fast.

The only problem I see with your wish list is that you won’t use the wheel enough. My response would be “ why would you spend money on nice wheels and tires and leave them in the basement?” Life is too short to ride shite wheels and tires.

I switched to 5000s on my Jet 5 and 6 rims and have used them for about 9 months. I got my first flat last week when I picked up a huge drywall screw. I stopped. Unscrewed the screw (it was pushed into the tire all the way to the screw head), held my finger over the hole for about 5 seconds and that was it. I had just started my ride, so I went home and pumped the tire up to 80 psi and rode 50 miles on it with no issues and it doesn’t lose pressure. No way a 4000 With a latex tube and sealant would have sealed

I used to use latex tubes, generally were fragile and a PITA so were for race day only. Also I found they were quite sensitive to QC issues.

Now on Bontrager TLR wheels, tires and sealant, with good luck on the crappy pavement I often have to race on (including multiple race speed square edge hits that would have flatted a tubed set-up and ended my race). So for my racing, tubeless is the way to go.

Tubeless give you an incremental rolling resistance over clinchers with latex tubes. However, with the current crop of awesome tires (like the Continental 5000), that difference is relatively minor.

Tubeless is less prone to punch flats and can self-seal some punctures.

In my case, the gains are tiny. I rarely flat, and the the performance gain is so small it did not matter.

I did tubular tires many years ago, and I did not want to go back to the mess unless it was a huge advantage.

That explains why I have a set of wheels with tubeless tires (25) hanging in the garage. I figured it was time to change the sealant and I simply cannot get the freaking tires off. I lost all confidence that I could mount a tube in them if I did flat, and they are collecting dust now.

I'm going to talk you out of tubeless. For training purposes it's hard to beat a durable clincher unless you're willing to do the PM necessary with tubeless sealant. I mean... maybe you get a flat every now and again but changing a tube really shouldn't be a big deal for anyone regularly riding on the road. For long course tri I don't think tubeless is worth it compared to a fast clincher with latex tubes. In my experience, tubeless road tires seem to work about 50% of the time and the times they don't work you're going to either have to plug the tire (quick) or sit on the side of the road and struggle to get one of the beads off to pop a tube in. For short course tri I think tubeless is definitely worth it especially if you're chasing the podium.

MTB and gravel is a totally different story. Tubeless all the way.

I'm going to talk you into road tubeless, mtb tubeless, and gravel tubeless. Cyclocross training on tubeless is fine, but race on tubulars to keep the gods happy.

First of all, tires--like chains, cassettes, and cleats are consumables. Ride the hell out of them and replace them when they are worn. More miles without flats and then you can throw on a new set of tires every 2500 miles and get back to it. Do not baby them and try to save them for races. They are consumables and should be treated like toilet paper. Use it and throw it away.

Road tubeless is the future. See any cars on the road with tubes in their tires? No.
Road tubeless gives you the ability to carry less stuff and the tube stash can get donated to the local charity.
Road tubeless is just as fast, if not faster that tubes and can be run at lower pressures for added pleasure.
Road tubeless might take 5 more minutes to setup, but wouldn't you like to forget about pinch flats on the crap roads or broken glass shards all over the place?
Road tubeless does not magically make you superman and you'l still need to pick a nice line and avoid massive objects the best you can.
Road tubeless does require a little maintenance every 30-60 days as you check on your sealant. Good sealant won't dry out fast and leave you stranded. Do your research.
Road tubeless tires can still get cuts and be damaged, ride responsibly.
Road tubeless tires will give you more miles without simple flats due to faulty tube installations, punctures, pinch flats, or defective tube valve stem areas common with latex tubes.
Road tubeless tires will allow you to live a more green life, and all those tubes can stop ending up in the trash.

Gravel Tubeless - ever ridden on a real gravel road, the rocks are sharp and the lower pressures allow the tire to flex a little around them instead of puncturing. Yes you'll still need to use your brain and take a nice line, but they will save you more than they will hurt you.

MTB Tubeless - low pressures, more grip, duh.

No.
No.
No.

You listed the only positive.

They cost more. And are a greater PITA in several ways with seating, sealing, getting a puncture and spraying goo all over, etc. And I rarely get a flat where the sealant would do any good.

Obviously lots of opinions out there. I honestly wonder whether the tubeless fans really ride their bikes all that often. I live in an area with tons of very serious cyclists, lots of pros and top masters racers, lots of people who do 10-20k per year, and can easily afford whatever they want. I don't know a single person who uses road tubeless as their regular setup. Yes lots of us have a set of tubeless wheels set up for gravel and road races with shit pavement, where there's some hope that it might seal and save your race (my races are over if I flat). And yes we all use tubeless for MTB. For regular road riding? Not worth it. I could see maybe going tubeless for TT/Tri races, but then I'd use corsa speeds only and I'd change the sealant every couple months, or you may as well not have tubeless anyway. If that hassle is worth it to you to possibly save a race some day then go for it. I've only ever flatted out of one TT (out of probably 100 total) and in that one I hit a rock so hard that the rim was destroyed, so in that case tubeless would have not only not saved my race, it could have been dangerous.

I actually cut off a tubeless tire once. I remember when I used to run tubulars and they were even easier to deal with.