CO would be your best bet. Without points, you can't draw a General tag in WY. The Special tag isn't even a guarantee anymore. But, the Special tag would eat all $1,000 of your budget just for the tag.
If you are determined to go, and it sounds like you are, go ahead and put in for some of the draw units that don't take any points to get. This is a good way to make sure your buddies are committed as much as you are. You'll all be monetarily bound. Check the box on the application that says if you don't draw, you want the OTC voucher. Then, you just take the voucher into any Wallyworld and exchange it for your OTC elk tag.