It all depends how you do it. If you get the Stan's kit, you start with the bare rim, but the yellow tape down which seals the spoke holes, then stretch their rimstrip over the rim, put tyre on and inflate. Ghetto's the same really, but replace "yellow tape" with electrical tape and "their rimstrip" with butchered 20" inner tube.
I've personally just found a selection of tyres to cover all eventualities and conditions that I know will seal with a track pump. In a team of 4 at Mayhem you likely have about 2.5 hours at least to change tyres, there's not a huge time constraint!
FWIW I'm usually near the 'sharp end' in these things too, although I'm not sure what difference that makes, if the technology's good enough for the top pros in the world it's good enough for a slow poke like me! You're less likely to flat than you are with tubes.
If you want to switch to tubes then you have to take your rimstrip out, it's a bit of a faff, but not a major issue.