Class A CDL questions and advice

I'm a weekend drag racer. I have been towing with 60-75' motorhome/trailers for 20 years. I keep reading about the gray area of DOT officers requiring racers to have CDL's. I have talked to both my state and FMCSA about this and am told I do not need a CDL, yet I have also talked to DOT officers that state I do. In trying to do the right thing, I'm trying to get my class A CDL with my Freightliner Columbia conversion motorhome and 38' gooseneck trailer, 72' total. I have about 10 hours into practicing for the 90 degree alley dock. The problem is that unless I get the trailer parallel before entering the cones, the rear overhang goes over the boundaries. I failed at this on my first test and the tester even told me I was using way to big of a rig for the test. I now have two more attempts. I was told today that I should use a dually and trailer exceeding 26001#, to get my class A combination, then take my single motorhome to get my airbrakes, my trailer does not have air brakes, but has a 16K# gvw. Will this work or will I just be restricted to a class B air brake vehicle? I'm not in this for a business, just looking for the simplest way to make everyone happy and not get in trouble. Thanks for your advice.

 

Thanks. I fully aware of the rules and I strictly follow question 21 on the FMCSA page. No sponsors, no offsetting taxes, etc. I have thoroughly researched this and feel I have a complete grasp of the black and white law, however, road officers interpret things differently and I'm just trying to keep the peace by doing my part.