It kinda blows my mind that they even make a tubeless valve stem that doesn't have a removable core. I don't get that, and have never seen it, but I won't argue with you. For difficult mountain tubeless tires, a trick we've learned from Notubes at our shop, to get the tires to seat, is to remove the valve core and inflate the tire with a compressor by putting the air directly into the valve stem without the core. This seems to put more air volume into the tire faster than with the valve core installed, and difficult-to-seat tubeless tires will almost always inflate using this method. Once that's done, and the tire is deflated, the tire should be easy to inflate because the bead is already in place more or less. But you would need a valve stem with a removable valve core to do that, and I really encourage you to use this type of valve stem with your road tubeless setup. I should also mention that with mountain tubeless we use soapy water on the bead of the tire.
I've not used Shimano tubeless-ready road wheels, but my experience with road tubeless so far has been that with tubeless-ready rims (Stan's Notubes Alpha 340's) and the Hutchinson road tubeless tires you mention, an air compressor is not necessary for tubeless inflation. Just get the tire on the rim, make sure the tire's bead is to the outside of the valve stem on the inside of the rim, inject sealant through the valve stem, and the tire should inflate with a floor pump.
We've done a few road tubeless "conversions" where we use non-tubeless road rims, tubeless valve stems with removable cores, Stan's yellow rim tape, and Hutchinson road tubeless tires, and these do require the use of soapy water on the tire's bead and an air compressor. Again, inflation with a compressor without the valve core and sealant installed before final inflation will help get the bead in place before you add the sealant and install the valve core. Then you're ready for inflation and the tire should seat.
As part of my emergency kit with road tubeless I carry a spare tube wrapped in a rag in my seat bag, and I carry a couple of small, thin strips of an old tire for a tire boot along with my other emergency items. The rag is for sealant cleanup in the unlikely event of a flat. The tire boot(s), always a good idea anyway, is a good idea in this case because if I were to have a flat, it would probably mean a good sized hole or tear in the tire has taken place (the sealant will take care of small punctures), and would require a tire boot to get home.
Hope some of this helps-
Last edited by well biked; 01-30-12 at 04:10 PM.