"One thing for sure, you will know every inch of the truck and will be so in tune with it"
Mundgyver makes a good point with this, and if you keep the truck long enough you'll be money ahead no matter how much you spend. With the way prices are and will be on new vehicles and the amounts in resale value lost the moment you drive a new truck off the lot, there's little chance that you could spend enough on this truck to equal your losses if you went through two new truck purchases over the next few years.
Mundgyver makes a good point with this, and if you keep the truck long enough you'll be money ahead no matter how much you spend. With the way prices are and will be on new vehicles and the amounts in resale value lost the moment you drive a new truck off the lot, there's little chance that you could spend enough on this truck to equal your losses if you went through two new truck purchases over the next few years.