So I definitely heard all of your collective advice.
Per usual, I do my own thing. LOL.
Haven't made any decisions yet, but taking a few minutes here and there to look at available options has been a great and fun distraction.
For context, we were supposed to do two short trips originally, as we've done before (not always, but sometimes) one trip closer to my bday, and one a week later, closer to our anniversary. It so happens this year both events actually fall on a weekend, so we couldn't go on the actual days with our Weekday Select AP's (which expire 9/6.)
Since we had a challenging year, I decided to go with 3 days at the end of August rather than 2 in August and 2 in September, and just splurge a little more in August. We were trying to avoid the Star Wars madness even though I love Star Wars. Hence the 8/25-/8/28 trip.
The biggest downside to that was missing Food & Wine, which we love. We had hoped to do a different luncheon this year, but even with more flexibility of dates, the only ones available are the ones we've done already. (That doesn't mean we wouldn't do and thoroughly enjoy them again, but my instinct would be to try to find something different first.)
Based on past experience (he's been looking for a job in some form or another almost every year for the last several years) it's a slow process. I think the chances are low that if we postpone the trip by a week, we'd have to cancel so he could start a new one. I mean, you never know, but I doubt it.
The rooms in general are only slightly higher that week. (Pop Century was like $5 more per night vs. the week prior.)
We would actually save money with the pup. Best Friends Pet Care is almost $40/day for day care (not overnight.) If we leave her home, we have a local sitter who comes to the house 3 times a day, and charges $20/day. I'd rather have her with us, but it's a short trip, and we won't have to spend about 90 minutes out of the day dropping her off and picking her up. I mean, it's totally worth it when we do it, but this will be our last park trip for some time, AFAIK.
I'm going to do a little more research, but we are really all about the dining at WDW. Given that, having a less expensive room and more money for dining and drinking (especially at Food & Wine) fits better, the more that I think about it. The fact that there is still availability at reasonable pricing is surprising (and fortunate.)
Going to check crowd calendars just in case. We'll see. Should make a decision by tomorrow.