Anyone else see a problem here??
I think you're one Cub short of a full barn. Time to start looking again!!
On the serious side, as you know, you really need to be careful when loading your Regular on a trailer. With the tread width of the tractor and the single hand brake, Farmall Regulars (and other F series) are a very dangerous tractors to load and unload.
What makes yours even more dangerous is the added width of the cut-off wheels which look like they were offset to clear the final drives. You may want to look for another set with larger diameter rims which would allow clearance for the final drives and less offset.
When I bought my Regular, I ended up buying a different trailer with a 102" wide deck. I'm sure the trailer you used also had a 102" width but it looks like a close fit. If you don't ever plan on transporting the tractor you probably don't have to worry about it, however, if you will transport it....
Anyway, great looking tractor!! Keep us updated with pictures as you work on it. Oh, one more thing. If you are going to paint the tractor, tighten the frame (box tubing) connections at the rear end, motor mounts, radiator mounts and the front bolster before hand. If not tight they will flex somewhat and damage your paint job.