Transitioning from Singles to Doubles

If you're good at seeing a variety of combinations and how they work out you'll be better at doubles, and if you're good at planning how to weaken things to win later you'll probably be better at singles, i think
This. I still consistently play Singles (LC, NU) but I'm actually a lot better at Doubles in the short time I've played it because I have an easier time making a variety of combinations and being able to abuse two Pokemon on the field, while in Singles I tend to overpredict due to 1 vs 1 situations.
 
That's why the comparison to chess, so often made, doesn't work for singles, as never in chess is there a strict one-on-one matchup to exploit. However, doubles is very similar to chess due to the nature of having to protect your pokemon from a variety of attacks from a variety of positions on the field, making it more exciting in general.
Can people stop comparing Pokemon to chess? In chess you do not play your move at the same time as your opponent, you take it in turns, so there is no "prediction", which is a key part of all Pokemon metagames. In addition in chess, you have perfect information, that is, a queen is always a queen, with exactly the same properties, but your opponent's Garchomp could be Banded, Scarfed, Swords Dance, etc, so while you always know what your opponent's queen could potentially do to you, the same is not true for his Chomp. Thus chess is a game where you are more in control of your own fate, even excluding the existence of hax in Pokemon. In chess, if your opponent makes a mistake, you can exploit it and win. In Pokemon, if your opponent makes a mistake, you can actually lose out because you predicted he would do something sensible (eg, you anticipate a switch because your opponent can be OHKOed, so you make the appropriate double-switch, but your opponent stays in, sets up anyway and proceeds to flatten you). This brings into question what even a "good" or "bad" move is any more (maybe your opponent was expecting you to overpredict and wasn't being stupid), and it becomes a game-theoretic exercise in risk/reward and Nash equilibria. In chess, everything is certain because the moves are not simultaneous, and moves can be rigorously declared good/bad by extensive analysis.

I actually think of singles as far more chess-like, due to the ability to see a few moves ahead, and the game revolving around probing the opponent's weak points until you have a winning combination, and then executing that combination (and this is, at higher levels, precisely how chess games are won). The 1v1 match-up issue you mention is a fallacy: Pokemon is a game of 6v6 and, Shadow Tag aside, you are never forced to lose a 1v1 match-up, because you can always switch out, even if that means sacrificing another Pokemon (and this is like chess too: there will be times when an opponent has you in a corner, such that, whatever you do, he is getting a winning position). I don't know about you, but I can never think more than one move at a time in Doubles, because so much can happen in a single turn, both in terms of variety and impact of outcomes, that the situation must be constantly re-evaluated, and a new plan formed, after every turn. I think if Doubles is like anything it is the board game Diplomacy (Google it), in that moves are made simultaneously, and the game won mostly on whether or not you anticipate your opponents' moves, complicated by the fact that the game encourages you to declare what you are going to do beforehand, but not necessarily truthfully.
 

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