I can't say it bothers me at all really, unless I'm really unlucky and something gets announced in a slightly better version only a couple of days after I have purchased the older version. But I blame something like that on personal bad luck more than anything else.
Fact is, I'm a collector, and as such I collect purely for the enjoyment of it. So the only value that matters to me is the personal enjoyment I get from owning whatever it is that I choose to collect. Monetary values of what something is worth if I were to sell it doesn't really figure into my personal mindset, and everything I have purchased was done so at a price that I was willing to pay at the time. If someone gets the same thing cheaper down the line, good luck to them. Doesn't affect or bother me one way or the other. After all, in my own time as a collector I've gotten my own share of great deals, just as I've also paid above retail for older pieces that I really wanted, it's all part of the deal as far as I'm concerned. And at the end of the day I've paid what something was worth to me at the time in order to own whatever the piece is in question. Whatever may happen in the future as far as re-releases or superior products being made goes doesn't change or invalidate that, nor does it diminish the enjoyment I originally got from owning said piece.
To me, my collection isn't an investment, it is purely a collection, and the money that I have spent on it is money that is gone. The money I spent was done for the enjoyment I get out of owning the pieces that I own, and as I am careful to only buy what I really like and want, I have already gotten my money's worth (unless a production piece turns out to be a dud or whatever) .
Sure, I can see the point of view that if I ever were to sell anything that it would be nice to get back what I paid, or even make a profit (then again I can say the same thing about anything I own), but honestly, that kind of thing is merely gravy to me, it is not why I collect, has no bearing on what I collect, or how long I keep it for. I'm not judging those that do put importance on percieved monetary or market value, it just isn't a factor to me personally. So re-releases, edition numbers and sizes, and the like just don't have much impact on me and the how, what and why of my personal collecting choices and habits.