Sometimes good players will be worth more as teams in the hunt will be looking for a solid player to pickup. Then again, it probably evens out a little as teams also hold fire sales. For Div V you should be able to get a decent guy at a decent price any time of the season. My advice would still be to invest in your arena now, keep getting management experience, and try to win your division next season or the season after. It's easy for me to say in Div III, but there's no rush. The best thing you can do is play the game more and read up on the game as much as possible.
I wish there were pigmen. You get a few of these pigmen walking around I'm looking a whole lot better. Then if somebody wants to fix me up at least they could say, Hey he's no pig-man!