I agree that it sucks, I haven't played this game yet, will though, looks like an easy 1000 and i love Madden games, (considering doing the 30 years achievement without simming, but I'll see when I play for a while.)
But my brother tried explained this to me on the cap number, (he's going to school for video game design) because I've noticed this number as a cap in many games. For example, rupees that you can collect in the original Legend of Zelda, Star Ocean games have a level cap of 255 as well as Infinite Undiscovery, madden 04 and NCAA football had a score cap of 255 as well, etc....
I believe what he was saying was that it has to do with the space of a byte. Since 256 is 2 to the 8th power and there are 8 bits in a byte, that would create a cap of 255 since you start counting at zero instead of one.
I didn't ask the significance of the powers of 2 and why it's calculated that way, but it made since. I believe that what he said the significance of the number 2 was that it is the highest number value that takes one digit in binary code.
I assume that the significance of raising 2 by powers is as simple as multication which would raise the value the quickest within the space of a byte.
I'm not sure if that is the exact explanation that he gave me, but it made since.