Just my perspective as someone relatively new to the hobby. One thing I like about pinball is that I expect that the pins I own will hold their value if they are good examples of good games. Ten years from now an Addams Family will still be a fun pin to play, it will have a cache, and they are not making new ones. Maybe pure players are okay with remakes but collectors want original. That said, the older mediocre games I think may fade. I owned a Jokerz and it is pretty cheap ($1400) but it is also not that much fun next to a new game. However, I still play my Whirlwind and Taxi from the same era and think they are great fun. Sometimes you want a complex game but other times you just want a fun shooter. Having a mix in your collection is great.
I currently own 7 pins (SimpsonPP, Indiana Jones PA, LOTR, Taxi, AFM (orig.), Whirlwind, and Dr. Dude), except for maybe Dr. Dude I think these will hold there value (maybe some will increase). I have been tempted to buy new but I think I will lose money. I have considered a new Avengers but don't want a Pro and the LE seems pricey. Maybe more importantly, I am not sure how fun they are. I am sure an Addams Family will be fun, it has proved that over 20 years but a new machine, who knows.
I also like to restore pins and those are really hard to find. Almost all the older pins seem to already be restored. I think there was a wave of broken down machines like 10-15 years ago when a bunch of arcades failed but now I don't see them.
Lastly, Colorado is kind of in an island so you really have to jump on good pins locally. I have a 1000 mile search radius and ended up getting LOTR in Ohama and SPP in Nevada. I could have my pick of pins if I lived in PA but here seems like a sellers market.