Thanks so much for the post and pics, we have a ADR for our Dec. trip. We are celebrating my inlaws 50th Wedding Aniv. there and hope to have a window seat to watch the fireworks. I mentioned this when I made our ADR, should I call again a week or so before we leave? I can't wait to try some of those dishes. I can see I will have issues making up my mind. Thanks again!
You note that you will be there in December. Some weeks are really SLOW and some are really BUSY. It is easier to accommodate requests during slower periods. Since I almost always make my reservation for 5:30, I always get a window seat. During slow periods, Wishes is at 8:00 - which means you can book for 5:30, enjoy a leisurely meal and, if you take your time, still be at the window seat at 8:00 when Wishes starts. This assumes you are working in concert with your server - that is, that they know what you are trying to do and are collaborating with the pace that will get you there (otherwise, they will go at restaurant pace - each course following the other fairly efficiently). There is also an unwritten "rule" that if you occupy a table for more than 2 hours that you tip higher to make up for what the server lost by not turning over the table. You probably already knew that, but not everyone who reads these posts may be familiar with US tipping customs and I don't want be accused of giving advice that hurts the servers financially.
I prefer a windowseat because I like to take food pictures in natural light (no flash). That is really the primary reason the CG food pictures are so superior to most of my other food pictures (although AP and GVTea also have natural light, and therefore beautiful pictures). I don't actually care if I am sitting for Wishes - once again, my preference is to be on the balcony - so I can take pictures without window reflections from the restaurant. See - different "requirements" call for different plans!!!
If you want to be sitting at a window seat during Wishes, you need to start with knowing when Wishes is scheduled for that date (sounds like December schedule is posted on Disney's site from a previous poster's comments) - and back up from there - including a buffer for additional wait because you can't register your request until you checkin at the podium on the second floor, therefore, you cannot fully predict / control how long you will wait.
Recap:
- The only way (that I know of) to guarantee a window table without a wait is to book for 5:30, then check in as early as 5:00 pm.
- The only way to have a window table under other circumstances is to check-in early at the podium for your reservation and be mentally prepared to wait (maybe you'll get lucky and not have to...).
Some people just don't like eating at 5:30 - too early. It happens to be my preference - I like the window table, natural light for pictures, glorious sunset, and casual transition to Wishes on the balcony (in early December, anyway). But as I made reference a few posts ago, we have done multiple scenarios, and the are all wonderful - there really aren't any bad choices, and "optimal" is in the eye of the beholder.
Click here for multiple scenario recap
In response to your other question - I would guess that 95% of the time, my reservation requests are present when I check in. That said, if it is important to you, it doesn't do any harm to call a week out and have them read your requests back to you to make sure they are present. Then reiterate it at each customer service contact point (podium check in, restaurant lobby checkin, server greeting, etc.) until you are convinced they've "got it".
Did that answer your questions - or create more confusion??
I look forward to seeing your photos as I continue reading. 
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