Just wanted to chime in with my pre-trip experience with the DSS CMs and first time booking CLFP for our upcoming January trip. I did read up on the various CLFP topics here (thanks so much to everyone who has posted!) and felt pretty prepared. The CM I spoke with when I booked in October was very knowledgeable and super friendly, and I felt she would have been able to give solid advice if I was completely in the dark about CLFP.
We booked the trip 91 days from our checkout date, but it took me the rest of that evening and most of day 90 to speed-plan FP and dining. I called DSS just after 9 am Eastern on a Monday, 89 days from our check-out date. I got through to a CM immediately, and the process took maybe 20-30 minutes (I was only booking 3 days of passes). The CM booked all 6 FP for us on our CLFP days, and she was able to get everything at the exact times I wanted. We had to cancel our Halloween trip just a few days before, but the FP I had booked with those now-canceled tickets were still showing up in
MDE and creating error messages when the CM tried to book the January FP (even though we had completely different tickets for the new package). But, she was able to get the obsolete FP removed and everything showed up correctly in MDE very quickly.
We booked a couple of regular FP at Splash on our CLFP days, and of course a few days later the Splash refurb for Jan 2020 was announced and fell on most of our trip, which then bumped our second Splash FP. Since it was a regular FP I could have waited until my 60 day window to modify it myself, but I decided to just get it out of the way early. I called DSS back and got to a CM after only waiting on hold for a min or two, and was able to get the new FP for something else very easily.
Last week, we decided to flip one of our MK and EP afternoons, which involved changing around part of one of our CLFP days (we have 2 CLFP booked at HS that morning). I cancel our regular MK FP and started rebooking at EP, and there was decent availability at all the EP attractions including Tier 1 (this was over a week after my 60 day FP window). I was able to get 2 of my 3 regular FP for times sort of close to what I wanted, but for some reason there was this weird donut hole with NO FP availability at EP of any kind, any attraction, any tier, from like 1:30 pm to 4:00 pm. I tried clearing my browser history, used Safari and Chrome, used my phone's browser, used the MDE app on my phone, but still could not get a FP for anything at EP to show up. At that point I decided to deal with the last regular FP later and called DSS to deal with switching the third CLFP. This was my only real wait dealing with DSS so far, on hold maybe 10 minutes right around lunchtime on a weekday. The CM was able to switch my 3rd CLFP from MK to TT at EP, and was once again able to get it at the exact time that I wanted, even though that time wasn't showing up for me in MDE.
I mentioned the weird afternoon gap and asked the CM if she could check to see if she was also seeing a lack of availability. She said she was able to see plenty of availability, asked me what I was looking for and when, and was then able to get all 3 of my regular FP at EP moved to the exact times and rides that I wanted (again, those times did not appear for me in MDE). So I don't know if there was an issue with my computer or MDE, if I just happened to luck out on FP times opening while I was on the phone with the CM, or if the DSS CMs are allowed to sort of force the system to book FP for CLFP guests at times when there might not otherwise be FP availability. Either way, the DSS CMs were able to solve every random FP problem I've had in the last month or so, and every interaction I've had with a DSS CM regarding CLFP so far has been excellent.
It was also really nice to have fewer days to worry about booking when the 60 day FP window opened. In hindsight, I might have been a good idea to do all our CLFP days at the very beginning of our trip to make it easier to book headliners for those days. I tried to space them out a little over the week and put some low-key, sleep-in/resort-heavy days in between them, just so we don't burn out halfway through the trip, but they would also be really helpful earlier in a trip. I don't know how often we would splurge on it in the future, but for this particular trip, I'm already really glad we decided to buy those 3 days of CLFP!