Tons of real good info here. I'm going to agree with Gdetrailer. That would be a lot for a first timer. First thing I'd do is buy more pickup than you need. I know that means different things to different people. One should never feel like they spent too much money or that it's a waste of money to to have a 3/4 ton diesel while towing a 24' trailer. First off, a you'll not likely recover the cost of a diesel, so I'd toss that idea out the door. The advantage is effortless towing at 1800 rpm up hills. I tow completely effortlessly with my rig and I love it. I've pulled a 30' trailer(up hills/down hills, no matter) with my pickup and it's equally effortless. Though I don't think anyone that has never towed really "gets" how much better a diesel is towing, I don't think they need to go thru the "gas rig stage" prior to getting a stout 3/4 ton. Please take this with a grain of salt. After all, it is just my opinion. My dad had an RV shop for many years and I've been towing since I got my license. I've not been without a trailer since I was 22 years old. To me, diesel is to towing, what fuel injection is carbureted engines. Both work, one is much easier than the other.