I am currently a PS4 user and plan to buy the Xbox series X and thus I plan to have TSW2 for series X. However, I have several pieces of TSW2 DLC on my PS4 and I'm not sure if I can redeem those with my Dovetail account on Xbox Series X or I have to pay for them all over again. Though the former seems inconvenient to the Dev team, the latter would be a hard hit on my wallet. I don't care so much for Penninsula corridor, LIRR and CN Oakville subdivision, but for East coastway, Tees Valley Line, Main Spessart bahn and HRR, I already bought for PS4 and have yet to play. Can somebody give me the answer to this question: Can I carry over DLC that I bought on PS4 to Xbox Series X? (And I'm not talking about the main game here.)
You can‘t. You buy the content for one platform. Keeping your content when switching from PS4 to X Box Series X is not possible.
You won't be able to carry over your DLC, bought on a Sony games console only plays on a Sony games console, same goes for anything xbox dude, no cross company platforms.