Yes and No.
It will really depend on what pins you buy and in what condition.
Stern are moving to LCD quite soon so will these recent, very expensive pins start to look dated?
I think it could be hard to get money back on all these LE editions.
However we lose money on all other consumables, tv's, phones, hi-fi, cars.......pins are expensive toys so yes, if you buy 'wrong' and are buying to 'invest' you will more than likely take a hit.
Buy games that you love playing, in the best condition you can afford