My limited knowledge of tubeless:
I am running ghetto tubeless on my Jabber using gorilla tape. My front tire is tubeless ready on a stans rim, back is a normal WTB on a non-tubeless rim. No problems so far for 1.3 seasons.
Mounting is the biggest hassle--much more so if you are not using tubeless ready tires and rims. With a tubeless or tubeless ready system, the sealant is basically just acting as a filler when you get a flat. With a conversion set up, the sealant also needs to actually "seal" the membrane of the tire so it can inflate. Using soap suds on the beads to help them into place works well. Be sure to use a air compressor or high capacity pump. I have successfully used a pump with the tubeless ready tires and stands rims. If you are having problems with getting the beads to set in, I found that inflating to a low pressure and then pushing on top of the tire with the wheel on the ground and can help the bead "pop" into place. Its also important that both the rim and tire bead are clean before you mount. Using rubbing alcohol to clean has worked for me.
Re: sealant, I use the basic "home-brewed" recipe from MTBR and it seems to last 6 months or so before hardening up into a booger. I am not a fan of the stans, as I had 2 punctures it did not fix last year. If you go the home-brewed route, a little extra latex mold builder in the formula seems to help seal up conversion tires.
If you want to save money on an injector, go to your local walgreens and ask for a couple of baby syringes ..they work just as well.
Now, of course, I am destined to get a blowout on the next group ride.......