Thank you all for the advice and input!
We ended up booking at Dolphin for check in on May 28th, and check out on June 3rd. When usi g points the only option of room I got was standard with 2 doubles, but they went ahead and gave us late checkout at 4pm (which was alreadfy a Gold perk.. so no big win there), but also asked us if we wanted to request early check in at 7am. Right now we said yes, but wanted to ask all those that might know... would such an early check in time be detrimental to our goal to upgrade to a better rrom with either a bigger set up or nicer view? We did go ahead amd request one of the following rooms if available: 8015, 7015, 6015, 5015, 4015, or 3015. These rooms came as suggested rooms to request from TouringPlans site... but can't really confirm if they're all that great or not.
Basically, would we be trading in the ealry check in for the potential to wait and get a better gig?
We really wanted to make October work, but because we'd need to check in by 9/30 at the latest, and that may not jive with my work, taking DD4 (will be 5) ouht of school for a week during her first month of K.. and the previously undisclosed fact that we may want to start adding to our Family of 4 sooner than later, we ended up booking for May. We'll definately loom at an October trip, probably for 2021 for WDW's 50th. At that time we think we'd more strongly consider taking kids out for all the newer stuff that won't be there this year)