I tried the winter start and it's rough, not being able to get to level 20 to get stats above 200, not starting with enough gold to get forge early enough for winter because you need gear upgrades cause axe with 200 stats is not great vs the new enemy that seemed to spawn 80/90% of the time at least for me, but we managed, the worst thing though is probably is having to go through all of Lucy's dialog again such as the dialog about undeads after defeating a skeleton even though Scout is already in her romance progression, or when you talk to her about her options such as her interests, beasts, or how she became a mage to name a few, but I dunno, these were just things I found annoying, being half way into winter with rarely anyone to visit the inn making it hard to earn money for upgrades or even to get the forge. It felt really bad when the dwarves would show up and offer meterials but I have no use for them cause the forge was several upgrades away. Started in Fall and had the forge and all stats at 300 with a fully upgraded katana and 2 upgrades of the armor after plate.