Also in Vancouver, on a pretty aggressive road bike and I'm running 25s. The roads here are pretty good. Bigger could be nice, but honestly you're fine with what you have. When you tear the tire or wear them out then you can reconsider.
As for tubeless... I find flats are significantly less of an issue on road wheels. I maybe get like... 1 a year. Having to deal with the mess of tubeless for that, for me, is just not worth it. Could it be more comfortable (see lower tire pressure), sure, but I'm not uncomfortable, so I don't bother. Also easy enough to change a flat.
If you want to go for a road rip, hit me up. Roads are pretty damn quiet these days with the whole 'rona thing going on. Trying to stay off the mountain bike as I've proven in the past it's a really good/fast way to hurt yourself.
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