I think it is going to work this year as long as the weather is good. Wife, baby, and grandma are going to FL for 5 days in January. I'm willing to make that drive but the weather's gotta be favorable.
My personal opinion is that you just go for it that week. Plan for it and if you get up there and they didn't get pow then knock out some UP resorts like the Porkies or something just to notch those on the bed post.
That way you're not stressing it. Either you get to slay Boho of you get to pop someone else's cherry.