Company Vehicles Equal FMCSA Compliance Obligations

A CDL license is a federal license that is issued by the state where you live.

https://www.fmcsa.dot.gov/registration/commercial-drivers-license/drivers#Classes-Licenses-Commercial-Learners-Permits" rel="nofollow - Drivers | FMCSA (dot.gov)

Even though you may not consider yourself "commercial", it doesn't mean you aren't. If you are doing anything for compensation, you are commercial. We had a local guy that has a race car and has a dually diesel pickup with an enclosed triple axle gooseneck trailer (well over 26,000 pounds). Since he is eligible  to receive prize money, he is considered commercial and must have a CDL to operate legally. 

There are some exceptions for operating farm vehicles for yourself.

The "gray area" comes in for non-commercial vehicles over 26,000 pounds. Non-commercial vehicles are regulated by the state and vary from state to state. If you cross a state line, it is your responsibility to know the regulations in the state you are operating in.

If you own an RV over 26,000 pounds, you are probably non-commercial (unless you use it for business) and wouldn't need a CDL, but New York requires an "R" endorsement on your regular operator's license. 

These are NY State regulations:

https://dmv.ny.gov/forms/mv500c.pdf" rel="nofollow - Driver License Class Descriptions (ny.gov)

Best thing I did was not go with a one ton dually/40' dual tandem as the 30' behind my 3/4 with Firestone air bags has worked out very well.

Run from KC and east, do not do DC or south of FL panhandle and basically camp out in OH. Plenty of trips to Chitcago and Indy and run up to Detroit more than I care to as MI roads are the worst with their short pour slabs. DOT and ELD guidelines can drive a fella crazy and you can get different answers in each state when going thru weigh stations as it seems things are being tweeked slightly all the time.

Will do it until I am not able to tarp taller loads, seeing the country again and having a ball.

What is the GVWR on your Trailer ID Tag?  and the GVWR on your Truck?  Then Combined?

PJs sales add is deceiving, that Pete sitting on their Gooseneck Trailer behind a single wheel ton is WELL Over GROSS Weight for CDL , the Peterbilt Truck By ITSELF is 18,500-20,000#, then Trailer and pickup, I doubt they are UNDER 6,000#.

Had a chuckle when the dispatcher told me how much I was rated for on loads he would be booking when I signed on, had to explain trailer rating with trailer weight deducted from trailer gross and told him it did not matter on overall gross per DOT at 26K as I would limit trailer load(s) to my trailer specs.

I.E. just because I am rated to 26K max per DOT, does not mean I am pulling loads for more than the trailer is rated for, plus I have a safety factor built in to boot.

Most of my loads, say 90%, run 6K and below and it is a unique market we wanted to try vs. the dually one ton with 40' dual tandem where those boys run partials. See many going down the road with a partial on the front after dropping the rear partial, no weight on steer axle and flogging it. Have helped a few young guys on the roadside or behind weigh stations that flat overloaded themselves and got in trouble. Nothing like seeing a one ton dually blast by that is overloaded, only to see him headed down the other side of a pass in West VA and both rear duals come off the trailer axle on one side. I'm right there with Wal-Mart rigs as I run 67 mph most anywhere, slow and steady wins the race and the ELD dictates how much we can drive anyway so I don't flog it. When a big rig screams up behind me, I just get over and pass them headed up the next hill, with 3.73 gears the Cummins is a bear on hills. Hard on the fuel bill, hard on the equipment so learn how to drive with the engine brake settings and tune in to my favorite old country channels on satellite radio. 6.7 Cummins running on Schaeffer's oils, HotShot Secret for fuel treatment and use that engine brake in tandem with adjustments to the brake controller. Wheels all come off truck and trailer for a good inspection every time home; just hung new springs, drums/brakes, equalizers and greaseable pivot bolts under "2021" model trailer that went out last July and was knocking on the door of 100K miles. Take it easy and do the maintenance to make everything last but will not go back out next winter as far to hard on both me and the equipment. Will lay down mid December this year and head back out towards the end of March as I grew up in that salt crap in the northeast and I don't need the work that bad. MO has not bothered me but I am usually in MO very little, headed to the barn after staying up in WI, MN and Iowa and winding my way back down with loads that ultimately bring me back to DFW.

Plenty to do on the farm in the winter anyway, plus there is all those A-C projects that have piled up!