I'm not sure this would accomplish what you want. Losing over and over will likely discourage some people......ask Flap

. Adding money to it is also likely to end the fun pretty quick. Giving away your best plugs also wears thin at times. What might work better is for some of the guys who use the forum the most to each contribute a plug or two to be raffled or auctioned in the main forum. That money could the be split into quarters. One quarter to the site off the top. One quarter to a plug contributor picked at random. Next, the mods pick 10 plugs from all the plugs that are posted here (not the raffle plugs) over a time period (say 6mo to a year) and we vote on the best in 2 catagories......experienced builder and new builder. The winners get 1/4 of the raffle procceds each. I think that might encourage people to post their plugs without making it a direct competition. Enough people win to keep people happy, but without big money involved.
Another idea that I'd like to see is some sort of swap that encourages use of the plugs. For example everyone involved could be paired at random with some one else, make one plug to trade to the other guy, then you've got to go fish the plug you get (1 week window). Guy who gets the biggest fish on someone else's plug wins. The losers send all the plugs to him and he and the builder of the winning plug divide them up. Of course we might have to give a positive poundage to handicap whomever has to give Eddy their plug to fish....but it would probably work out seeing as Eddy's plugs work better than Eddy. Something to consider, anyways.
Another idea is a flavor of the month thread. Each month or two we all build one type of plug (say a needle) and post a picture. The viewing public can vote on a winner, the guy with the most wins at the end of the year gets some sort of small prize/recognition at the plugfest (the sillier the better).
Finally, I'd suggest we do away with mega swaps. This, I realize, may not be popular but I think it kills a lot of participation on the site. Guys end up building tedious numbers of one specific plug that takes all winter and keeps them from experimenting and posting different stuff. Difficult topic, since a lot of people have built up a big plug collections by participating in these swaps, and no one forces anybody to be involved in them, but I do feel their impact on the site deserves discussion.