Starting up. Intersting situation.

I drive a 99 379 and love the older trucks. A couple of the problems you can run into are that some insurance companies will not cover them and some places will not let you lease on a truck that old. Another problem is that if some idiot totals it out you will only get fair market value. They don't care how nice it is or was.
I paid $28000 for my 99 and a 48x102 flatbed trailer in 09. At that time it had less than 100000 on the inframe. Not saying anything bad about the truck or even that it isn't worth it but if you are going to make it in this business you will have to be smarter than that.

 

here's the problem with that half a mile statement you made. you mean your dads 5 mile to a gallon truck is worth it? my truck on a bad day gets 6.8 miles to the gallon. feds tax you by the mile at 5.5 miles to the gallon. which means you think that monster engine is going to only cost you about $9000 ish more to run but here is a break done on fuel costs alone.

25000 gallons of fuel at 5 mpg. $98750 per year for fuel.
22727 gallons of fuel at 5.5 mpg. 89771.65 per year for fuel.
18382 gallons of fuel at 6.8 mpg. 72608.90 per year for fuel.
16667 gallons of fuel at 7.5 mpg. $65834.65 per year for fuel.

Actual costs for you to run just in fuel is $33,000.00 leaving out the fuel tax. As I do not know how to calculate that. but basically that is the cost of the pretty truck versus a high fuel efficient truck. Even my truck would still cost you $26,000 less in fuel then the pete. fuel prices were calculated at $3.95 a gallon. This also assumes your truck can actually get 5 miles to the gallon. Good luck. By the way I do not own my truck I am a company driver.