As a diesel performance enthusiast, I recommend the following:
Early Duramax. They have great track records. The Chevy trucks that surround them tend to have some reliability issues; mostly electronic. Don't be surprised if your CD player defaults to max volume everytime you turn on the key, but most owners (according to a JDPower survey) didn't find them annoying. Comfy interiors and great ergonomics are a big plus.
1994-1997 Powerstroke. These are not to be confused with the earlier 7.3 turbos... make sure its a powerstroke with the direct injection. There is nothing wrong with the older 7.3 and 6.9, but they are very old-schoool and don't need to be discussed. These early 'strokes don't have an intercooler, but the 215 hp they provide is backed by a buttload of torque that is very nice. I used to full-time RV for three years towing 10,000 lbs with a 1995 F250 powerstroke. It made it through Beartooth pass, crossed the rockies 7 times, made it from Phoenix up 8000 ft to Flagstaff a few times, and never missed a lick. I documented 110k miles of towing 10k lbs in that truck and the only thing I ever had to do (aside from normal maintenance) was replace the glow plug relay. They're a common failure item. Put your foot to the floor and top the hill at 75 mph.
1999-2003 Powerstroke. Along with the redesign of Ford's superduty line, the 7.3 got an intercooler. Nice upgrade. I love the trucks, but in-depth engine repair gets expensive. The new body style means that if you need to replace a head gasket, you have to basically pull the entire cab off the frame. But the engines themselves are awesome, reliable, and powerful. Any added stress or expense fixing problems is offset by the significantly upgraded powerstroke engine.
6.0 powerstroke... don't really consider them. Most of their bad reputation comes from turbo problems, but for someone who wants a dead-nuts reliable truck you might steer clear.
5.9 Cummins: 1989-1992 they used a 12v cummins with a VE rotary pump. They are reliable, simple, mechanical, and wonderful. They won't win any speed contests, but can be very easily modified to make great towing power. 1992-1998 was the same basic engine but they used a P7100 injector pump that is called the "holley carburetor of diesel engines." Its easy to modify, super reliable, and makes great power when modified. 1998.5-2007 cummins are 24v and use an electronically controlled VP44 pump. They have the same mechanical reliability as their predecessors, but the VP44 is VERY sensitive to the fuel volume it gets from the pump in the tank. When the tank pump starts to go, there is a good chance you'll fry the VP44 which is a $2000 repair at best.
But... my editorial commentary on the subject is this... If I could get a cummins engine in a truck with Ford's build quality and Chevy's ergonomics/ride quality, I would be a millionaire. I like ford trucks, dodge's use of the cummins, and chevy's extensive devotion to rider comfort.
This also depends a great deal on what kind of horse trailer... if its a 2-horse trailer then you can tow that with a 1/2 ton. If its a 6-horse trailer, then we're talking something bigger. I will let you in on my latest truck purchase; I am a diesel freak, so when I needed a truck I looked hard for an early cummins, an early Dmax, or a 7.3 PSD to fit my $5000 budget. The best I could find was a 1994 234k-mile cummins for $4400... well under NADA value, but I ended up buying a 120k-mile F150 gasser for $4500... also well under NADA value. As much as I wanted a diesel, the current pricing in my area combined with the price of diesel made me consider (and buy) a gas truck.