First off I am a ford diesel enthusiast.
My pick is a 99-00 F-550 crew cab, manual trans,12'-16' wooden floor stake body dump (4x4 if you ever drive off pavement)... this will be my next truck.
F-450 is like a F-250 gonna wish you had the 550 or 350 for weight ratings.
I own an 01 F-350 4x4, reg cab, srw, diesel, auto trans, leveling kit w/35" nitto grapplers and 18" kmc addicts that draws the eyes. I tow a bandit 90 (4500lbs) or a 12K dump trailer right now. Often there is a 2k lbs ramrod mini-skid with a branchmanager hanging out in the bed. I have had a "nice looking" 4yard box built with load handler to chip into. The trans I have is made by BTS, last trans you ever buy; unlimited hp, miles and lifetime support. I have replaced 3 transmissions. Should have bought a BTS first time. Engine produces about 300+wrhp currently with tuner intake and exhaust as apposed to 190+ stock. I have run about 60k miles on veg oil, best diesel truck engine by design to run wvo out there.
this gen of 7.3l diesels are legions in numbers. That means parts are common and well priced if you shop around. Lots of after market performance out there.
the 03-07 6.0l gen is not as bad as some make it out to be. Problems are known and fix kits are available for about $1300 w/out labor to address the heads and egr issues. Because so many are all about the 7.3 and the 6.0 has a bad rap super deals are to be found. Tuner, intake and exhaust yer playing around 450rwhp.
the 08-10 6.4l twin turbos are awesome. Early release regen glitches got solved with tuning. Highest reliable hp gains for any diesel for least amount of coin. Intake, exhaust and tuner yer pushing 550rwhp, sorry cummins. Big boys are making 1,000hp
Yupper F-550 crew cab. I would say manual trans just cause how much time and money it takes to deal with auto problems. If you could find a truck with a trashed auto for a song buy a BTS and be done. Just saw F-550 crew cab landscaping dump on ebay needing a trans, at $5k no reserve going to go for less than $10K. I would say be suspect of mason dumps and trucks with plows, they tend to be used a bit harder. I'm dreaming about a 26' knuckle boom behind the cab(weigh 2klbs and cost $10k new) with a 12' flat bed/6'stake sides dump.
I do not know where your at but in NY I can tow up up to a 16k trailer with my 9990lb gvwr F-350 with out a cdl. A F-550 with a gvwr of 18k can only to a 8k trailer before cdl. A chipper in NY falls into the equipment category so there are no weight issues, although some troopers might not agree.
Engines for the 7.3's are everywhere for about $2k-$3k used, around $5k built. Regularly last to 300k miles. Of the 99-03 7.3's that were made, the best ones are the late 99 to 00 due to forged rods, supporting up to 450-500hp. 01-03 7.3ls had powdered metal rods pmr's known to shatter around 400+hp.
Want to learn more goto powerstrokenation.com
it's like the tree buzz for ford diesels