Advice: There is a safe option so that no villagers will move out while tting. This is possible after a villager has notified you that they are leaving. After that villager has pinged you, save and quit, then you can use your clock to safely time travel to the current date without losing any villagers with this huge time jump forward on your clock.
To answer the poll: It would depend if I have the beautiful town ordinance on or no. If no, then I would have to go day by day. If yes, I would use the method above, and go straight to current date. Recently, I had been very busy and missed a couple days of play. Yet, went day by day because the town is new and it's my first winter/snowman events and I don't have the beautiful town ordinance enacted. Otherwise, I would have skipped to current day and not play the days I missed.