Don't know where you'd find a Shadow for $1500? Aren't they upwards of 2 grand now?
HS2 is fun, but simple - doesn't fit your criteria. I don't care for the video mode either. Same thing as I500 pretty much. FT has the best video mode in the history of pinball by a long shot.
TFTC is pretty fun, but the Cryptkeeper can be annoying. Has a lot of features for the price (cool ramps, cool modes, 6 ball multiball, shaker motor). Wish I could get to Crypt Jam but I suck.
I haven't had my JM for very long, but let me tell you, this game flows. I have a hard time getting into it because of the crappy theme though. I actually watched the movie to understand it better and now I think I like the pin even less because of it. Also, if you have broken plastics or ramps other than the left one they are pretty much impossible to find. Not sure where you are seeing them for $2500 other than eBay, but I'd gladly sell mine for a thousand (good luck finding the right ramp it needs).