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1.) Enable the Winter, Liz Katz, and Doja Cat DLCs and start a new game.
2.) Run M1 / F1 to M13 / F13.
3.) Run the Liz Katz guide (1 to 4). Start it by going to the front door and choosing Open. She should have been waiting there since early on in the game.
4.) Run M14 / F14 to M45 / F45. During this whole time Doja Cat should be banging on the backyard fence, just ignore her.
5.) Run the Doja Cat guide (1 to 4).
6.) Go back to a previous save (maybe M43 / F43) and run the Winter guide to get the two achievements. You may be able to get the two Winter achievements after completing the Doja Cat guide, but I am not sure if you need to hit the Game Grumps with a snowball? They will no longer be there after you do the Doja Cat guide since they left in M45 F45.
This is what I just ran and was able to get all the Winter, Liz Katz, and Doja Cat achievements. Hope it helps.