Going tubeless? I hears it's pretty awesome and I look forward to trying it out this winter to help traction in the winter slime(sleet and snow). But it isn't without it's issues, the big one for many is inflating and seating the bead. IT requires a burst of air pressure. Car tires and many small wheels(dollies wheelbarrows) are also tubeless and the trick to seating the bead is a matter of a spritz of hairspray and a match(Google it I'm not sharing it because boom).
Another option is to use an air reservoir that holds a certain volume of air and is released all at once as apposed to how your bike pump works. Here's a video that explains how to build your own.
#bikehacks #hacks #video #badass