Anything “pickup” is out, you have reached the limit of even an F550... ...assuming machines or steel means heavy equipment or farm equipment...
I have a Freightliner FL60 and it will pull in that range and higher. The brakes are rated for 40K on the frame. Any of the “baby semis” Freightliner FL50/60/70, Ford F650/750/850. GMC & Chevy Topkicks C4000 & up, etc. will work for the application.
Now the next problem. The trucks I’m talking about weigh around 12K to 15K aand your load is 20k, now add 7k to 10k of trailer weight. You are talking about 40k or more going down the road. The Federal limit for non-CDL drivers is 26K. I pull a 13,600lbs 5th Wheel Trailer with a 13,300lbs truck and have about 4,500lbs of cargo. I’m moving over 30k of RV down the road without a CDL, BUT, should I ever get weighed I get a ticket. They mostly ignore RV’s, but not heavy equipment loads. Also, both the truck and the RV are under the 26K so I am in a slightly gray area not being commercial.
Next problem. You are talking a HEAVY pindle hitch (equipment) trailer or 5th wheel type semi trailer (lowboy) to handle that weight. A gooseneck might work but most are rated at 26k and weigh 7k or 8k themselves; add the 20k load and you are over their weight rating.
Problem solved? If you have everything farm tagged you are golden...
Sum it up... Even to rent a truck & trailer in that size you will need a CDL unless you get a farmer friend to help you out. A contract load on one of the “haul my stuff” web sites might be the best way to go. If you are going to do this several times a year it might be worth getting the CDL and a truck; the used ones are fairly cheap.
An F550 diesel will get it done. They are rated for somewhere around 25k towing. Maybe more.