What tow-rig to get?

Keep in mind, that 90% of my towing would only be 50 miles tops round trip (once or twice a month in the spring/summer...and maybe once or twice during fall), and maybe one or two trips to Richmond (2.5hrs) a year.
$5,000 is my absolute maximum spending limit. 4x4 is not a must, but is highly suggested. I would be parking in wet/muddy fields a lot, and could use it for winter.
Anyways, I've got a dilemma. I've always wanted a M35A2 Deuce and a half (go ahead and laugh). Mainly for show, but I could also easily tow the Bronco with it. Car shows and parades would be so fun. I'm a member of Steel Soldiers and have done quite a bit of reading on them. I know their maintenance needs and costs fairly well. Plus, I could use it around the house...Mom is always bugging me for loads of mulch or rock (1/4 of our property is flowerbeds).
There is one here in town that I can have for $3k. Needs a pinion seal. Thats it...great paint, no rust, runs excellent and is in very nice shape.
Now the practical side of me is looking for a F250/350 to double as a DD/tow-rig. Because of my price range, I'm looking for a decent '92-'97. Found a F250 in excellent condition in SC a few days ago. Ex cab long bed 460/5-spd/4x4 with 118K on it for $5k. I found several more for $4k-$5k, but haven't heard back from anyone yet.
One thing I have found out about these trucks, is that they are either ragged-out former work trucks with 250k miles on them or more for cheap, or they are in mint condition and the owners want $10k+. There really is no middle-ground.
If I got the pick-up, I would have to sell the 'Yota to help pay for it.
If I got the Deuce, I would keep the 'Yota as a DD. Gas prices will eventually go up again to record high's, and I don't want to be stuck with a 460, or 7.3L when it's $5/gal. I learned my lesson when I had my '97 F150 that got 8-10mpg's.
So what say ye all knowledgeable FTE'ers

I'm also considering a 1st or 2nd gen. Dodge CTD/5-spd.
In all honesty I would look at the 92 through 97 Fords like you are doing. I think I would narrow it down a bit more and go with a Powerstroke instead of a CTD. The 460 5 speed sounds like a good setup. The SC long bed makes for a really nice ride thanks to the long wheelbase. The tradeoff with that is it takes a fair amount of area to turn. I had a extended cab long bed for 5 years.
The 1st second gen CTD have a great engine. The rest of the pickup I am not such a fan.











