Bear in mind that any pin can get boring if it's the only one you have and you play it all the time. Assuming that this will be your friends only pin then I'd make the following comments on your revised list (these are just my thoughts and your mileage may vary):
HS2 - Not a huge amount of depth and you'll see all it has to offer pretty quickly but it's the kind of game where that matters less than others and is actually not a bad game to have on it's own.
JP - Lots of modes and decent ruleset with a wizard mode at the end so something to get your teeth into and should last a while. To me though, this is a game where once you've done all that you'll probably want something else (a bit the opposite of HS2 I guess)
Demo Man - Lots of multiballs so if that's what you're after then this is a good one but another with a reasonably shallow ruleset. It's a bit like HS2 in that even once you've seen everything you'll still want to play it but I think HS2 is the better of the 2 games.
T2 - Bit of a 1 shot game this and shallow rules again which I don't think it survives well as an only game. Great in a bigger collection but my advice would be to steer clear of this for your first.
Road Show - Loads of stuff to do and loads of modes so will last you a long time. Modes are linear so can get a bit boring playing the game in the same way each time but there's other stuff outside of modes to go for so not too bad. You get a lot for your money with one of these. The country music that plays during multiball is sh*t though.
Judge Dredd - Kind of similar to Road Show in that its got a lot of stuff going on with modes, multiball and other bits and pieces so another game where you get a lot for your money. I'd definitely say to try and have a go on one first (tbh this applies to all of them) as it can be a bit marmite.
