I"m not a satellite expert and don"t play that many, however the situation you describe seems relatively akin to a standard STT.
Personally, I think that consistently making the last two/three, and getting your money back is not a bad thing. Reaching the cash bubble with a shortstack is a pain, but better than being the wrong side of an early gamble, and not cashing at all. That early gamble might bring you to the bubble with a monster stack, but even then that is no guarantee that you will win.
If this were a winner takes all tourney, then I would advocate the early gamble and playing for the win from the start..... but when a third of the field is getting a prize, ICM comes into play a lot more as it would in a conventional STT, and making the money becomes imperative.
Keep plugging away, you"ll get there Matt.... don"t see cashing as a bad thing though.
I"m sure someone will respond now and tell me this is crap..........