Do you need a CDL to haul your own equipment?
There is no my-own-equipment exemption in the federal rules, so owning the machine does not decide it. The federal CDL classes apply to vehicles used in commerce, and hauling your own machine to your own job is usually business use, which means what decides is the weight test rather than whose name is on the title.
That is the trap in this whole subject. People hear commercial driver's license, read it as driving for hire, and conclude that a contractor moving his own skid steer between his own jobs sits outside it. That is not what the phrase covers.
What does use in commerce actually cover?
More than hauling for pay. The federal rules reach vehicles used in commerce, and running your own machine to your own jobsite is business use of that vehicle even though nobody is paying you for the drive. The truck is working. The line the rule draws is not between your machine and someone else's, it is between business use and everything else.
The Equipment Hauling Fit Advisor asks whether the use is commercial and then refuses to let a no close the question. Its own note says it straight: hauling your own machine to your own job is usually business use, so answering no there does not settle it.
Then what does decide it?
Weight, through two tests, and either one can apply. Group A under 49 CFR 383.91 is a towed unit over 10,000 lb paired with a combination at 26,001 lb or more. Group B is a single power unit at or above 26,001 lb GVWR, towing or not, which means a heavy enough truck raises the question with nothing behind it.
Both tests read ratings and actual weight. The commercial motor vehicle definition in 49 CFR 383.5 reads rating or weight, whichever is greater, and GCWR counts as the greater of the manufacturer's rated value or the sum of the unit GVWRs. Three separate paths to the combined number, and every one of them counts. The trailer end of that is worked through in does a 14,000 lb trailer require a CDL, and the definition itself in what GCWR actually limits.
Where do the real exceptions live?
With your state, mostly, and they are narrower than the rumors that circulate on jobsites. Several states issue a non-commercial Class A or B aimed at exactly this situation, private hauling of a heavy trailer, and that is a state license class rather than a federal exemption. A state may also waive farm vehicle drivers operating near the farm under 49 CFR 383.3, which is a conditional waiver tied to the farm and the distance, not a blanket pass for anyone who owns a tractor.
States move the other direction too. A state can be stricter than the federal floor and can apply its own rules to intrastate driving, so the answer for a haul that never crosses a state line is a state answer, not a federal one.
What should you do with this before your next haul?
Get your own numbers before you go looking for an opinion. Truck GVWR off the door jamb, trailer GVWR off the VIN plate, the manufacturer GCWR out of the towing guide for your exact configuration, and a scale ticket for the loaded rig if there is a scale within reach. Run them and see which lines they touch. The advisor does that screening and prints a brief you can hand to a dealer, a rental yard, or your insurer, and it sits with the other buyer-decision tools in the Rethink tool catalog.
Then take those numbers to the people who can actually answer. This page is a screening aid, not legal advice and not a licensing determination. Your state can be stricter, can apply CDL rules to intrastate driving, may offer a non-commercial Class A or B, and may waive farm vehicle drivers operating near the farm under 49 CFR 383.3. Confirm with your state licensing agency, and tell your insurer what you are pulling while you are at it, because the license question and the coverage question get answered by different people.