As I understand it the CDL requirements are national (someone correct me if I'm wrong), so what is going on in Wisconsin should apply.
The last time we got dragged to a scale (and passed, btw

) we had a few minor things we had to repair before they'd let us street the truck and trailer again, so I also had to run out Emergency-51 style to do the repairs. Taillights and wires was all, but during that time I was asking the trooper about trailer requirements. This is what I was told by her, and another at another weigh station, and the state's manual corroborates this (and I posted that part of the manual somewhere here):
If your trailer's GVW is less than 10,000 pounds, it doesn't count toward your GCVW. It's like a freebie. Now, if you're overloading a 10,000# trailer and something happens like an accident, you're probably going to be toast for overloading the trailer.
When the trailer is at or over 10,000 GVW, it counts toward that 26,000 magic number. So if your trailer has a GVW of 15,000, to stay under the CDL requirements, the vehicle towing it can only have a GVW of 10,999 or less (and be rated for a 15,000 pound trailer).
Possible scenarios:
Guy is pulling a 20,000 pound trailer(GVW) with a 5,000 pouind truck (GVW). No CDL required. (I know someone's going to freak out at this one - please go check your states regs before posting to disagree with this one.)
Guy is driving a 20,000 (GVW) pound truck with a 7,000 (GVW) pound trailer. CDL not required (the trailer is less than 10,000 GVW, so it doesn't count).
Guy is driving a 16,000# GVW truck, pulling a 10,000# GVW trailer. CDL required.
I think Chevy's 3500 HD trucks were tweaked over the last few years, sensitive to this issue. Most skid steer trailers have a GVW of 10,000 or more (though we have one with a GVW of 9,900), and their trucks (at my last check) have a GVW of 15,500.
So as long as you don't have the biggest skidsteer on the market, you can get truck, trailer and skidsteer to a jobsite, legally under the 26,000# GCVW CDL limit.