Ten foot poles are useful things, however I am not going to touch the topic of "should I or should I not use tubeless" with one today. Instead I will spend the entire time emptying my bag of magic tricks for working with tubeless should you be so inclined.
Nearly all of the wheels we build include tubeless compatible rims. The RCG36 and GX24 series are notably tolerant of a bunch of different tires and just don't burp, while Easton R90SL builds can be touchy to inflate but then don't burp even at super low pressure. HED Belgium+ are inflation tolerant and brilliant at burp avoidance except at super low CX pressures. Stan's rims are usually quite easy to get inflated, but tires can fit really tight on them. Boyd rims usually need an extra wrap or two of tape but then they're good. It's not that straightforward, but as ever we're here to help.
Caveat number one: For mtb tubeless, use whatever the heck tires you want. For CX and gravel tubeless, tubeless ready tires generally work way better. For road tubeless, don't even try without tubeless tires, as regular beads will eventually blow off and the potential for personal injury is huge.
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Our wheels come wrapped with two wraps of tubeless tape, except mtb wheels which get wrapped with just one wrap. These wraps perform the function of sealing the spoke holes against anticipated air pressure. Usually but not always, they are what's needed to get a good tire fit.
Instruction number one: Inflating your tires for the first time WITHOUT sealant is smart and saves mess and shame later. Sealant is for final seal and puncture sealing, not for initial inflation and seating. I prefer sealants that you can inject through the valve, and that's the way I do it. If you use a sealant which can't be injected, you'll have to take one bead partially off to dump the sealant in the tire, but if the tire has already inflated in your test then at least you know that goodness and not badness and shame awaits.
If your tire almost wants to inflate, remove the valve core and re-try the inflation method. That will often do it. Once the tire is inflated and seated on the rim, take the pump head off of the valve stem and plug it with your finger. Then quickly sneak the valve core back in. You'll lose some pressure but with practice this is a cinch. You can use the special tool to remove and retighten the core, or you can use a needle nose pliers. Either way.
If your tire has no interest in inflating, you need a tighter rim to tire fit. You can try more tubeless tape, or you can break out the heavy artillery. From my considerable experience, the interference that the tape provides is almost entirely useful for inflation and does not prevent burping. Just having a super tight tape fit doesn't turn any old rim into a mack daddy cross tubeless rim. But it makes inflation easier. From my experience, the duck tape/gorilla tape solution is more often needed and more often viable in mountain bike situations. The only wheel I can remember using this on in the last few years is my RaceFace ARC rim/Continental X-King mountain bike tire combo (which really needed it, but works great).
The new "tank" floor pumps work well, by delivering a huge shot of air all at once. Quite often, that rush of air will provide just enough push to create the critical amount of interference to start the tire inflating, and from there you are off to the races. 90% of the time I use this sucker I need to do it with the valve core removed to achieve success.
If you have a few extra bones, a compressor is a nice tool. You only need a super cheap one and they can be had for around $50. Some come with a version of a crappy pump head on them, which you can replace with a good pump head. We have a Prestaflator here at the shop, and it's the bees knees though it cost more than the compressor did.
The corner gas station almost always has a compressor. This is how I inflated my mtb tires for years. Just take a presta/schrader adapter, put it on your valve, put the quarters in the slot, and go. Be VERY careful with pressure. A guy I know* once blew a tire off a rim and covered himself in sealant for not being careful.
If you are going to a race or you have a race team and a fancy tent and a hot dog grill to put in your fancy tent but your fancy tent doesn't have power to run a compressor, you might want to invest in an air tank to take to races. You can fill it at the gas station or with your compressor, and it holds enough to inflate a whole mess of tires. This one costs $30 at Harbor Freight.
I really never use soapy water anymore. Shake the wheel and go for a short spin around the block. If your tire is going to seal, that will seal it.
Sealant replacement interval depends on an horrific alchemy of dew point, sealant type, tire pressure, the barrel price of Brent Crude, and the birth rate in France. Better too often than not enough.
*It was me. It was me.