SST is really fun IMO, and a solid title. (Many friends also like this game.) And it's in your price range. Shadow is pretty cool too, but it's pushing $3k+ these days, generally.
(broken record impression) OK, in this range you gotta consider WPT. Do you like Steve Ritchie layouts? Howzabout Keefer rules? Chris Granner music? WPT has 'em all! Do you like depth? WPT is one of the deepest pins ever, and I would argue it's the most 'strategic' one, shot by shot.
Flow? WPT has it. Drop targets? SIXTEEN (count'em!). Nice open playfield that won't intimidate novices; subtle strategies to learn and exploit over time. A mini-playfield that is challenging and also requires precision. The main (non-drop-target) shots are tough, as the ramp and orbit entrances, and trough, are all located pretty high up the playfield. It will make the closer ramps/lanes on other games seem easier after a while.
OK, I'll give it a rest now.