@edd considers going tubeless:

Q2. How annoying is tubeless setups for commuters? Had a real comedy of errors with tubes during daycare pickup, including the mini pump pulling out the valve core on the spare, that I'd like to not repeat ever again.

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@ascentale @edd @bikenite A2: I find that tubeless setups lose air more quickly than tubes, so you might have to top up the air more frequently. Also the sealant that tubeless setups use will dry out over time. I have to put fresh sealant in about once a year. It can be hard to install a tire tubeless without an air compressor because you have to pump a lot of air quite quickly to make the initial seal. I think you'd find these inconveniences of tubeless more worthwhile if you get frequent small punctures. Tubeless setups are good at dealing with those. The valve core problem, though, will probably happen with tubeless valves too.
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@evn @ascentale @edd @bikenite somewhat related how much air do your tube tires lose? i feel like when I am away for work and don't ride my bike regularly they lose air more but that might just be a misperception. I feel like I need to add air somewhat frequently (like every 2.5-3 weeks?) #BikeNite
@genex @ascentale @edd @bikenite I would estimate I lose something like 2 PSI per week. On a mountain bike where I run low pressures (~25 PSI) I top up the tires once a week. On a commuter bike where exact tire pressure is less critical I inflate to ~40 PSI and top up about every 3 weeks. #bikenite
@genex @ascentale @edd @bikenite This will vary with tire type, temperature, sealant type, and maybe humidity.
@evn @ascentale @edd @bikenite interesting - thanks for the info!!!