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Pokemon will always be popular, but it fades from super popular to kinda popular and the prices seem to follow.
I think we're definitely on the downswing right now but we'll see how the red/blue focused movie does in terms of public interest. Prices went up with Evolutions, the 20th anniversary, XY and GO so there will probably need to be something of that magnitude.
If I were you I would invest in X/Y and ORAS copies right now because they're dirt cheap and will naturally increase in price when people get nostalgic for them in a few years. Probably not by a crazy amount, though.
Regarding the TCG Burning Shadows is probably what most people will say but I feel like it's the thing everybody is hoarding and as such won't be as valuable as some of the underprinted/more interesting sets.