Allan,
Yes I have a compressor for first inflate – it makes things much easier.
I'm not running ghetto really – Stans flow rims which hold tyre beads very nicely, but the tyres are non-tubeless, and I don't need a rimstrip for this particular pair.
Also, I only took them to about 22 psi, at which point I could see solution around a couple of the screws. If I'd have pumped them up too high, there would probably have been latex spewing everywhere, but since there was only enough pressure to force it to migrate down the hole it was fine.
Tubeless solution is, after all, exactly for this purpose.
They're off the bike again now, since I felt they needed more studs, which I'm part way through, but I'll post up about keeping air when they're back on.