Hey John,
I just got another trailer and went through this same thing. I finally got a hold of a higher up in the Harrisburg PSP DOT dept. (who happened to have a max wedge car I learned through conversations with him).

The skinny he laid out for me lines up with what I read:

You need a Class A license if towing:
-GCWR is over 26k OR
-Trailer GVWR is over 10k

Class B is necessary if a single vehicle (not towing) is over 26k

So my trailer I figure will be around 11k loaded, truck is 8k, and the trailer is rated for 15k GVWR, so I need a Class A. The trailer GWVR is the trigger that throws me into Class A territory.

http://www.dmv.state.pa.us/driverLicensePhotoIDCenter/license_classes.shtml

You do not need a CDL to do this, just a non-commercial class A (though the test is the same). He stated if the truck and/or trailer is in a business name as opposed to your personal name arguing the non-commercial fight may be hard, but if in your personal name non-commercial is exactly what you need. Also, according to the DMV over here in June the Class A Non-comm/CDL test is going to get way more difficult, so I'd do it before then.

Hit#2 is plating your truck. It will need to be plated for the actual weight of the combined set-up. So for example in my scenario, 11k trailer +8k truck + 2k misc (people/coolers/etc) puts me at 21k combined, placing me in a Class 8 (438 bucks a year, woof).
http://www.dmv.state.pa.us/pdotforms/mv_forms/mv-70s.pdf