I don't think anyone has the definitive answer to this - it seems to vary with whoever you ask.
However, it is definitely okay to make requests (I believe MS ask if you have any requests when you make the booking), it's just that you might stand less chance of the requests being met if they are doing room allocation on a first-come, first-served basis and you check-in late in the day.
In your case, as you'll be coming from the BWV, would you be able to check-in early and hope that your requests will be met?
That would be my choice too . I don't like carrying the cases up to the top floor, but I like it when we get there!
On our last trip we ended up about as far from HH as we could have been (despite a request to be nearby ) but it honestly wasn't a problem. I think I'd be happy with any location now as I don't think there's anywhere in OKW I really wouldn't want to be.
We haven't stayed at OKW before. Our 1st DVC trip was to our 'home' - Boardwalk. I would love to give all the DVC places a try so this year we are doing 14 days at BWV and 4 Days at OKW. Next time I would like to split our stay with VWL
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