After realizing that what I have mind is no where near cdl requirements, that being a 10000 gvwr 2500hd and a 9800gvwr trailer, another issue was raised about medical card, dot #s etc..
All I am going to be doing is PERSONAL stuff only! No money will ever change hands, not going to be for hire, or rent blah blah!!!
Most of my towing will be within 20 miles of home, but there could be a chance that I would need to travel out of state to pickup something up. Do I need all that DOT mess regardless of what I do?

 

I know in my state (South Dakota) there is no requirements for personal use until you get over 26k gvw

 

You should be Ok. I have a class A CDL with a few endorsements and its for a vehicle greater than 26k and a trailer thats greater than 10k