I pull with a 97 F-250 powerstroke extended cab. This is plenty of truck. My trailer is a full deck 18' car trailer, two 3500 lb. axles. It has trailered many full sized cars(Galaxies, Lincolns, Impalas mid-60's versions) all over the Southeast. It is marginal for the 3130 w/ loaded R4's, LA513 FEL, and bushhog. I'll go the less than 20 miles to my local property. I wouldn't begin to put it on the interstate to my retirement property in Tennessee. I recommend an equipment trailer of at least 8000 lbs. I'm not sure what my whole rig weighs, but I know I've towed big Lincolns and the 3130 w/ attachments is right up there in gross weight.
My bushhog is a "Bushhog" brand, Squealer 60" model. This has a stumpjumper and slipclutch, plus a 65 hp rated gear box. These are essential for my purposes. I also have a Bushhog brand boxblade w/ insertable teeth. I think other brands of Bushhogs like Woods are just as good but pay the three-four hundred extra and get the premium brands/models. All the knowledgeable people I have relied on have told me this is much cheaper and less frustrating in the long run. I'm a welder/fabricator as one of my second careers. I can't think fixing a lesser brand bush hog would be worth my time. Unless you're better at this than me, I don't think it would be worth yours either.
By the way, years ago I lived on a farm in Varina, Va., just down the road from Chesterfield, isn't it?