The pattern that has developed for Pokemon generations seems to generally consist of:

• New Generation Pair (Red/Blue, Gold/Silver, Black/White, etc.)
• Third Version / Sequel (Yellow, Crystal, Black 2/White 2, etc.)
• Previous Generation Remakes (FireRed/LeafGreen, HeartGold/SoulSilver, OmegaRuby/AlphaSapphire)

Sometimes in that order, sometimes with the remakes releasing between the new pair and the third version/sequels.

I don't want to buy a new Pokemon game every year. I'd much rather buy one per Pokemon generation, which would probably mean one game every four or five years. So which would be the best choice going forward? The initial releases are the most popular of each generation. The third version is essentially an expanded, better version of the initial releases, so it seems like an obvious choice. But the definitive version of each generation's new games is released some ten years after that generation ends.

So, let's take this generation as an example. Would you have bought X/Y last year because they were the first ever fully 3D Pokemon games? Would you have waited till this year, hoping for ORAS? Now that ORAS is released, would you buy that or wait to find out about X2/Y2/Z? Obviously it would be silly to wait a full year after their release to finally buy ORAS. The community would be a lot less active by then.

The decision is made a lot more difficult by the inconsistencies in recent years. For instance, HeartGold/SoulSilver could probably be said to have been the optimal choice for fourth gen, with Platinum close behind. However, no remakes were ever released in fifth gen, so waiting for them would have meant skipping the whole generation. Additionally, it seems Black & White (the initial releases) are actually more highly-regarded than their sequels. Who would have guessed that the best games of that generation would have been the first ones?

Ka-pi96 said: I'd say go with the 3rd version. It's always the best version (with the exception of 5th gen which didn't have a 3rd version). The remakes are awesome, but if you are only getting one it should be the new one with the new region and all the new pokemon from that region. And when doing that you obviously want the very best version of it, so 3rd version

But, for instance -- is the best version of Kanto found in Yellow version, or in FR/LG? Is the best version of Johto found in Crystal, or in HG/SS?

Hell, for all we know Nintendo will start remaking the remakes soon. It's just about time for another iteration of first gen, to tie in with the series' 20th anniversary.

Well, that's the dilemma of course. But you'd get the best version of each region and story.

I mean, I never played any fourth gen games. Would it make more sense at this point to go pick up Platinum and give it a go or to wait 6 years or so for the Sinnoh remakes?

Pokemon games never drop much in price, it's damn near impossible to ever find them for under $30. GameStop sells Platinum for $45 used. So I'd say price shouldn't even be a factor.

I won't get the nostalgic feeling anyway if I never play the remakes, so that also isn't a factor.

Always the third version (Yellow/Crystal/Emerald/Platinum/Black2White2/Z).

Although, you really should just shell out the tiny bit of cash and get one of the remakes, too.

third gen then....... you usually get the best of both pair games...

I still say buy them all. You can't predict how Nintendo will do things from generation to generation. If anything, just skip the remakes, because those don't provide new experiences.

That extra tiny amount is actually doubling the cost.

And it's not so much about the money as it is my interest in the series. I just don't get excited enough for it to play each region two or three times. I'd rather play each region/generation once. An added benefit would be seeing actually quite large changes from one game to the next.

Well, the gen 3 and 4 remakes would provide new experiences for me, as I skipped those two in their entirety. As well as Black/White, so I'm very curious to see what GameFreak does for those in, like... 10 years...

I don't mean buy the game the day it comes out. Wait a year or two (or even in to the next gen) and buy it cheap on sale or part of a buy 1 get 1 free deal (if you are in the US, Toys R Us and Best Buy offer these a lot).

If you can wait just a year or two, you can get the remake for a lot cheaper. Also gives you time not to get burned out by the series.