Quoted from Lathroum:My opinion... I would rather have several pins than one expensive pin. Yes, the new pins have all of the toys and rules and blah blah blah... but they are also EXPENSIVE... for the price you can buy several older pins.
This is good advice when starting out, and holds a lot less risk, but I think space ultimately becomes a bigger issue than money over a long enough collecting timeline. It's harder to find a particular game near you on the secondary market than it used to be, which contributes to the higher pricing. There's something to be said for making the most of each slot, so start working towards putting together your dream lineup however you need to get there.