Scripting it is pretty easy. I think payb.tc posted a basic PHP script for making martingale bets on SatoshiDice in the main SatoshiDice thread. I'll dig up a link to it later if you like. It would be pretty trivial to adapt it to play your strategy.
Here's the thread about payb.tc's SatoshiDice bot:
https://bitcointalk.org/?topic=80245Thanks. Didn't even realize there was a script posted on here.
I think I'll give it a try w/ 5 BTC... and hopefully after I bust that 5 BTC, I won't play anymore. =p