Don't feel bad about the frame of reference thing, it really does take years of swapping a lot of different pickups, in combination with a lot of guitars and amps before you start to get a feeling for the characteristics of the whole thing. I've worked with a lot of pros and most of them wouldn't be able to tell if you replaced their stock pickup with something quasi-comparable from another manufacturer. And sometimes even when you know tone, you'll think you have a cool new setup until a week or two later, and your ears start to notice something isn’t happening, or something in your tone isn’t all there. I had that happen when I threw the current Petrucci Dimarzio rig in my old Shawn Lane Charvel, I thought it was the coolest rig until a while later when I realized it was actually kind of weak and hollow. The Mahogany archtop probably just wasn’t a good pairing with those dark pickups. But I’m sure I could have given that axe to any number of players, they could have done a gig with it and thought it was just the coolest sound ever. It takes a while to get the palette for tonal subtleties.
On the other end of the spectrum, it seems like you have people who imagine all kinds of thing in tone that probably aren’t even there. It’s like the old Penn and Teller bit where they stand behind a 5 Star establishment filling plastic bottles from the restaurant garden hose, and then go inside and have the diners compare the different types of pricey exotic water, and you see these people swishing the water and commenting on its crispness or sweetness, when it just came from a hose. I think some people do that with tone too. I’m a super-noob on these boards, but I can tell the people here actually hear tone and know how to get it.
Anyway, on the subject of your dilemma, you said you wanted something toneful that isn’t quite as malicious as your Painkiller, and I’m thinking the Cold Sweat would probably be good, from all I’ve read as well. I’m finding out (from my similar thread about Sykes tone) that the Cold Sweat is sort of like the Les Paul John Sykes Mahogany Dirty Fingers of the BKP world (which means it’s probably even better) so for your mahogany Dean I’d say that’s probably safe. Ceramic with organic tonefulness might be more what you’re looking for, rather than the tone I hear when I listen to clips of the Nailbomb.
Then again, I'm the new guy. Just my 2 cents.