Daron, It sounds like quite the adventure you had, and will be having in the future, with the diverse flock you got!! I'm glad I got to meet you and look forward to seeing the pictures you took at Crossroads!!
I would recommend putting all the Icelandic roosters together in their own pen and keeping the 3 hens separate until next spring. With only the three girls, they will be overwhelmed with so many boys. By spring, you can choose which rooster to put in with the girls and raise chicks from that group. Then you could remove that rooster and (after a waiting for the hens to raise those chicks) trade the rooster for a different one. Keep track of which chicks are from the first rooster and breed the pullets resulting from the first breeding to a different rooster. There seemed to be two dominate patterns to the roosters that Jim had in the raffle, so maybe you will be able to cull those down to the best (meaning nicest personality among similiarly colored guys) couple by spring. For example: Breed one of raffle roos to the hens you get from Jake's friend. Let them brood the eggs and remove raffle rooster #1, when the chicks are weaned, place raffle rooster number two with them. Let them brood again. The pullets resulting from the two raffle roos could be bred to one of the roos from Jake's friend. You will, of course, have a bunch more roos from those breedings. You probably won't be able to keep them all.....therein lies the problem all of us have......what to do with so many extra boys. Each of us has to figure that one out for ourselves.....