You have some great options there. I own a Dialed In LE and a Hobbit LE and there two of the best pins I've ever owned. The latest Hobbit code update puts the game on a new level, very impressive stuff. JJP has done an an incredible (industry best in my opinion) job of supporting code for their games. Ted Estes has mentioned that yet another code update is coming for Dialed In too.

I would say that the Hobbit with its latest code is now the most immersive and deepest pin ever made. I own a WOZ as well and while getting to SOTR is likely more difficult to reach then There and Back Again I find The Hobbit to be the more immersive game thanks to the newest code. You can still find used HUO Hobbits in the $6500-$7200 range but I think the game will be going up in value due to the massive update that was just dropped for it.

You do have a pic of the TNG Enterprise as your avatar pic which makes me think you are a big Star Trek fan? If that is your preferred theme I would go with that one, especially since you regretted selling your ST pro.