Newer trucks will have much lower maintenance and repair costs but your truck payments will be through the roof compared to used equipment. You can get an old truck for very cheap but you can easily pay more than someone buying a new truck—if you don’t work on your own truck. New trucks will start having as many problems as an used truck after around 350k miles.
If I had a lot of money, I would go with a new truck and pay it cash so I won’t pay a dime on interest rates and to be able to get a discount for paying it on the spot. Then I would get rid of the truck before the manufacturer warranty expired, which can be around 500k.
The other pro about buying new is that you can drive more weeks out of the year because of less breakdowns. Used trucks, if not maintained properly, can leave you without work for weeks every year. One week without work equals to loss of weekly profit plus fixed weekly expenses.
I am not a big pete fan either, and would just go with an older W 9 myself. I have been driving an 06 W9, and it is a far cry from ever being the truck my 96 is, and is not a keep forever truck. They build maintenence problems in all the newer stuff that you will never have with the older ones, just depends on a guys business model.