OK I hear ya Mike.
I was reluctant to give up the widowmakers because I had already purchased tires for them, but turns out the farm tire guy found a set of the same 20" wheels in the non-widowmaker version. I bought those from him to replace my mine. I'm also going to swap my widowmakers over to the c50 and take those 22.5s with me back to Arizona, so that I have the option to run those if I want/need to in the future.
Everything is all mounted up ready and waiting for me at the shop in Nebraska, so I think wheel/tire situation is handled.
If cab and chassis is only 6500 or so the trailer I have should be able to handle it. I'll double check it's rating, or if not I'll rent something to have as support. I know it makes more sense to just put the truck on the trailer the whole way... but I'm out looking for adventure

This place is great thanks for the input guys. So helpful.