Not sure if its running or drives. Do you have any idea on a number to stop at? 10% premium is on it.
What do you mean compared to the 2 headlight versions?
Pre 58 trucks all had 2 headlights.
1958/1959 had 4 headlights.
1960 also had 4 headlights, but was the more modern body style.
Finding 58/59 parts is harder than getting 55-57 parts because they have traditionally been less popular. They are making a resurgence now though, so the prices are up but the parts availability has not really caught up to that.
Based soley on the pictures, the body looks reasonably ok. It is complete, but has some damage. Fixing the arrow on the bed is a real pain in the euphamism. You can't really tell from here what rust it might or might not have. The dash does not look mangled, which is a plus.
The mismatched and non-original valve covers and coil mount would indicate that the engine has been messed with. Do you care about having an original engine? If so, then you want to check out the stamping on the block.
If it were me, I would probably put a top price around 4k if it didn't run and 8k if it did. That said, I really, really like the 58/59 body style but am considered a notorius cheapskate by my friends.
I bought a running, driving 58 about 18 months ago for $3500. It needs more bodywork than that one appears to, but it gives you an idea of what is available.