OK, I am thinking since you have to assemble the stroller anyway it is probably best to have it silkscreened too. This way we know it's permanent, and the iron-on's I briefly checked into were around $10 anyway, and that's not even custom. If we went the do it yourself route it would be cheaper, but then there is the issue of cutting it out and all. So for $20 I'm thinking send it in and let em do the work! Let me know if you'd like me to look a little further though, I know someone with a cricut cutter so that could be a blessing.
ETA- I remember my initial reason for wanting the new stroller- it would be available for my whole stay. Duh! The two we have now are available from day 2 on, which isn't a huge issue for my friend whose kids are older, but mine will be 3 and 5 so if I had one the first day it would be a huge help. We'll be at Animal Kingdom that day and they whiiiine!