Tubeless tires for cyclocross, gravel, MTB and road have made huge strides in the past few years; modern tires and tubeless rims are better than ever. The days unreliable of home-brew conversion kits are mostly gone.
New tubeless tires can still be a bit tricky to get seated correctly on the rim for the first time, however. To make things faster and easier, give these installation tips a try:
Folded tires stored in a cold garage aren't very pliable. Setting the new tires out in the sunshine (unfolded) for a few minutes makes them much easier to work with. In cold climates, you can hit them with a hair dryer.
To seat correctly, tubeless tires need to have the bead slip up into the matching "socket" under the hook of the rim. Friction between the rubber of the tire and the rim strip can prevent this from happening. Mix up a little soapy water and lubricate the beads before you attempt to inflate the tires. This helps them slip into place.
The core of the presta valve in your tubeless setup can limit the rate of airflow into the tire. To help our tubeless tires to bead up, we want to hit them with a ton of air volume all at once. Removing the valve core, temporarily, can help this process. Re-install the valve core once the bead is in place. Use a presta valve core remover to do this.
Stan's, Caffelatex, and Orange Seal are some of the popular and reliable brands. Good sealants help fill any gaps between the tire bead and rim where air can escape, and also create a "lining" inside the tire casing to slow the rate at which air molecules can escape through the porous rubber once the beads are seated.
Modern tubeless tires are shipped and stored folded. This can create small kinks in the tire bead that can allow air to escape during inflation or prevent the bead from seating. If you encounter this problem, try installing the tire with an inner tube temporarily. Inflating the tube forces the tire bead into the "hula hoop" shape to match the rim profile.
Give it a couple days, then remove the tube and you'll find the tire is now much easier to setup tubeless. To further simplify the process, remove only side of the tire bead to remove the tube, leaving the other side completely installed and ready for tubeless use.
While it's possible to seat some tire / rim combos using a floor pump, a compressor is much more reliable and there's much less sweating and swearing involved. No compressor? Get a friend to pump while you manipulate the beads into place.
Once you've got the tire seated, try to avoid breaking the bead in the future (for example, to add sealant.) A better way is to inject sealant through the valve core with a sealant injector.
I hope this helps you get the most out of tubeless tire technology. Good luck!