My only ribbon so far was in a challenge with 612 entries, and I beat 92% of entries in the recent best of 2006 challenge which had 705.
So I would have to say the bigger the challenge the better.
Hard to say, I took the averages of my top 10 and lowest 10 % finishes and this is what I got.
Top Ten% finishes
average %-98.3%
average submissions-276
best finish 1/153
0 challenges: 1-150
4 challenges: 150-250
6 challenges: 250+
Bottom Ten% finishes
average %-35.9%
average submissions-283
worst finish 120/133
2 challenges: 1-150
3 challenges: 150-250
5 challenges: 250+
Seems to not make a difference, interesting to look at though.
On average (among my 8 highest), I seem to enter challenges who have about 300 peeps participating. Seems strange, since I'm always plotting to enter the less popular challenge in hopes of sliding to the top, but it never seems to work that way...interesting question, got me thinking!