Is this bad or just what I have to expect?

[Hammerhead]

If by the "cups" you mean injector cups, there is really no way to tell unless you take the truck home for the night, drain the oil, remove the pan, and pressurize the cooling system overnight and look at the cylinders, inside and out, in the morning.
As far as the overhead, cams, etc., I have gone with my young buddy to look at a few trucks, and all the dealers now know if I can't pull the rocker cover, connect my laptop, and basically do whatever I want for an inspection the conversation is over and we leave. The one dealer knows I have a Chinese version of Inline/Insight so they won't let me connect mine, but they let me use theirs.
He's starting to think I don't want him to buy a truck. He keeps telling me to just sell him mine, then he'd be done...I keep telling him I don't wanna tell him everything I could find wrong with mine, as anal as I am I'd end up rebuilding the whole damn thing.