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I now have a 99 f250 7.3 with fairly low miles. I have found a pretty nice 2008 F40 6.4 Auto and really loaded with only 22K miles on it. I tow 11 to 12K about 15K miles a year. This 2008 is probably priced at least 20K cheaper than a new F450 6.7... Why shouldn't I buy the 2008? I can buy alot of diesel for 20K?
Nothing. Just that my trailer will top out at 14.5K fully loaded which is a little heavy for the F250. I don't load it that heavy. Plus I may go for a heavier 5th Wheel Toy Hauler in the near future... The 99 is really a great truck but the time has come to buy newer... Of course when diesel hits $5 bucks a gallon I might reconsider...
I'm a pretty big fan of buying used and letting someone else take the depreciation hit. Especially when you can afford low miles. You can afford more truck, and you're not gonna be upside down on it for so long.
I'd keep the 7.3. If the one you have isn't enough truck I'd look for a 7.3 F450/F350 or the like. Sure some have had good luck with the new diesels but it seems I talk to more that had bad luck than good luck. I will stick with the 7.3's which I hear considerably less problems with. Plus they get great mileage.