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If doing it normally is too difficult, I would try and find some items to make the game easier. This would include items that allow you to shoot more bullets, like the hip holster or the backup gun (both allow you to shoot an extra bullet with every shot), or items that allow you to safely cross gaps, like wax wings or the jetpack.
the not so easiest way: your bullets never loose momentum and they will always fly symmetrically (what i mean by that is if you shoot a bullet int a wall at a 90° angle,the bullet will always come back at a 90° angle, if you shoot at 45°, it will richochet at 135° etc). the bullets will also always fly at the same tempo unless you hold items that change your projectile speed. in other words: you have complete control over your bullets, therefore you need to play trickshot as if it was a puzzle. the minigame moves pretty slow, and gives you some elbow room to move in order to adjust your shots more carefully.
Also, Blocks: in case you din't know, you can richochet your bullets off of blocks 4 times until they dissappear. if you shoot them at red blocks, your bullet will be destroyed, together with the block. green ones richochet the bullet but are destroyed in the process and blue blocks are both indestructible and allow for unlimited richochet.
use all of this knowledge to find the perfect angle to shoot the right block at, at the right time to get the targets.
what you should keep in mind when playing winchesters minigame, is that you're esentially paying a discounted key to get a random chest, determined by your accuracy. doesn't matter how many targets you get, there's rarely a reason to ignore winchesters minigame, assuming your key economy is neutral/positive and you have on your floor a lack of B+ chests. so even if you don't get an S-Tier, you still got a good deal with just hitting B or sometimes C. Acing winchesters game also doesn't has much appeal ,aside from getting the achievement, because if you hit all targets, its still randomly decided whether you get an S-Tier or A-Tier chest, so don't grief over the last target you couldn't hit too much, because honestly A-Tier chests aren't that good. They are mostly made up of either high Tier B Items or low tier S Items, which gives you a little bit of a gamble with how good your reward will actually be.
or, the not so easiest way in short: just look up some playthroughs.