towing

I'm very new to the diesel world (and even the heavy duty truck world).  I currently have a busted 1996 Dodge Ram 2500, A classy Yukon, and a Honda Ridgeline.  None of these vehicles will get my towing done.

I have a Bobcat 863, and a tractor/bushhog that I will be towing on a somewhat routine basis to do odd jobs for friends and relatives.  I just purchased a 24' dovetail trailer thats rated to hold 14,000 lbs, so it's pretty heavy itself.  Bobcat probably weighs in at 9,000lbs +/-.

The questions I have are more of a comparison on what you guys think between trucks..  What are the pros/cons of Auto vs. Manual?  Would one better suit my needs?  Looking for the most comfortable, best towing truck to get the job done.

The next question, should I steer my search towards a 1 ton truck for the better suspension, or would a 3/4 get it done?  Are there any other benefits of a 1 ton truck that I'm missing?

I don't need frills and features, I have the Yukon for that.  I just want a tough truck to haul my toys around..  Any insight/advice would definitely be appreciated.  In my brief search I've been leaning towards a 99-06 F350, and a Dodge 3500 (same years).  

i run dodges for my towing lots of power and good mpg's and unless that bobcat is the 300 series or the old 200 up it is only about 6k. get a dually the drw will pull alot better. get a manual  
I burn more diesel and run more miles in a week the most of you people do in a month. ctds that have been used 97 3500, 98.5 3500, 98.5 3500,01 3500, 03 3500. those that are being used 06 3500, 07 3500. and yea these trucks earn their living