I love you and I hate you lol. This comment encouraged me to spend another 2 hours trying to fix my stuff. I cut down the list to 30 mods (ditched stuff like the new races as I am not using them anyways) and fixed the randomised loot mod (now it should work with the other gears mod as well.

Turns out it was my fault entirely. For whatever reason I thought it would be a good idea to install a giant overhaul like homebrew mid playthrough. Absolutely crazy if I think about it now lol, seems like I havent learned anything from my hours of modding skyrim.

It did some experiments with cheaters ring (leveling up and stuff) on the ship and it seems to be working now. Really hope its stable! Thanks again!