Personally, I'd book at a moderate (just a matter of personal taste -- to me, the differences between a value and moderate are things we really use and appreciate, and we tend to function well even when crammed into a small space with one another), but there are pros and cons to both:
- with 2 value rooms, you'll have twice the floorspace, more privacy, and twice the bathrooms, but "free" dining will only include the quick-service plan, so any table service meals will come at a significant out-of-pocket cost, and you may have to upgrade your ticket package to qualify -- plus as others said, you can request connecting rooms (or adjoining rooms, if you don't want a door between) but there's no guarantee
- with a moderate room, you'll have less personal space and more subdued decorating, but some nice perks (additional floor space per room, queen beds instead of full, 2 sinks instead of 1 everywhere but at CBR, privacy curtains/screens over the sink area, in-room coffeemaker), and the regular DDP, but you may end up having to pay more for your room (e.g, upgrade to a preferred category or a different view) and/or upgrade your ticket package to qualify
Either way, "free" dining will probably cost you some extra money out-of-pocket. I'd book the rooms you think you'll be most happy in (regardless of what promotions might be offered), and then once free dining comes out, modify your package as necessary to qualify, if it will save you money in the end.
...and as far as timing, we book close to a year out, to ensure good availability. I recommend that anyone staying on property and wanting to make ADRs book no less than 6+ months out, so they can take advantage of the 180-day window... and then once your reservation is made, start watching like a hawk for special offers to be released.
