Aaaaah… I went through all this over the weekend, and boy was it a pain in the arse!! But I did manage it so there is hope, and I only used a track pump…
What I found is that when the tyre is just sat on the rim before it’s inflated it just tends to sit away from the bead. Plus, on the tubes I had at least, there was a thicker rubber patch around the valve stem that tended to lift the tyre slightly around that area, so as soon as you start pumping all the air just pisses out.
I got round it using some nylon webbing that I had laying around.. you can get it for about a quid a metre at B&Q or similar. I then used this to pack between the rim and the tube for about 5 inches or so either side of the valve. This brought the tyre and the tube a lot closer together, although still not perfectly, but enough that a little squeezing got it inflated. Once I had some air in the tyre, just enough to keep the bead hooked in, I pulled out the webbing and the tyre sprung into place and seated perfectly. Then pump it up and Bob’s your uncle.
I also found that once you deflate the tyre to put the latex/gunk/whatever in, the tyre bead came away from the tube again, so I needed to use the same method to get them to re-inflate.
I’m beginning to think that maybe the tubes I am using are too thick, and that thinner ones would be better/easier. Am try some thinner tubes on the girlfriends bike soon, and see how they compare.
Had the first short ride out on the newly tubeless wheels today, and they worked fine… not sure what pressure to use in the yet though, the normal pressure that I run seemed a little hard, so some experimenting is called for I think.
Good luck with it…