trading it in
You'll learn how to plow with a stick pretty fast. Then you'll wonder how you ever did it with an auto! I've only plowed with a manual, it wasn't a pain at all. Was in an F-550 though, not by my choice
the diesel w/manual will outwork your v10 by so much you'll think it was a tinker toy. check into the diesel forums for more info regarding 12 valve/24 valve considerations, the 53 block, etc. Body wise there is little to no difference between 99 and 01, other than the number of years on the road and subject to rust (depends on where you live). If you want a real work truck, do it, but be aware there can be a lot more maintenance associated with a diesel, and it can run into big bucks if you have to pay someone else to do it. my brother in law used to complain that every time his broke and needed service it was a minimum of 1000 bucks at the stealer.
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If you buy the 99, replace the lift pump as soon as you get it (unless the previous owner has already done so). Don't take it to the dealer and let them put another POS lift pump on it. Take it to a diesel shop or do it your self. The couple of hundred dollars you spend doing this willsave you $2k-$3k later! Other than that, you will wonder why you didn't go with a diesel a long time ago.







