Bank-Roll, Field Size, Quantity

I dont know if this belongs in Probability or here, as the examples are strictly MTT based I thought that I would put it here.

On my way home from work tonight, I wondered the following:

-Say Player X is at the 90% tile in any given field at any given tourny (Basically he could enter a MTT with a buy-in for $1 or $1000 and the player base would not effect his play/effectivness/skill in any way, 90% anywhere anytime).

-Now, lets say that player was given $330, and he was given the choice of playing 50+5's with fields of 200 (10k pool each time, 27 paid, enough funds at start-up for 6 tournaments); or 3+.3's with 2000 player fields (6k pool each time, 225 paid, enough funds at start-up for 100 tournaments)


Lets say the players goal was to play 300 tournaments and gain as much $ as possible. Which method would be his best option? If he chose the 50's, what would his odds be of not placing in those first 6 matches?