Sparkky,
You will need a 22' or better a 24' long 12 ton or 14 ton trailer. The tractor outfitted will be right around 10,000 pounds. If you get an 8' cutter, you will need the 24' trailer to keep it all on. You CAN get a shorter trailer and tag the part that hangs over with a red flag. BUT, the filled tires will be farther back and can mess up weight distribution. You are probably into goose neck trailers as being the only good option for that weight as the hitch weight is getting up there for a bumper pull.
As long as the TOTAL weight of the truck and trailer are 26,000 or less pounds, you DON'T need a CDL. (at least here in WI, double check your state)
jb