Check in procedures at WDW

I have stayed on property about a dozen times and when I've arrived early in the day, I don't think I have ever had to wait until the official check in time to get into my room. Since online check in started, I have always indicated my expected arrival time and asked to get into the room early over other special requests. On my last visit in 2018, I arrived at Pop around 10am and my room was ready. We always book a standard view room. I don't know if room category plays a part in my success. No guarantees that your room will be ready before 4pm, but it isn't outside the realm of possibility.
 
We really don't care about first available, we are just scarred from the Disneyland Hotel. We checked in at 10 am and check in time is 4, and we didn't have a room until 6:30, after going to the front desk twice and being told 25 minutes AND we didn't get the tower we requested nor the view we paid for.
We basically don't want to get to Florida at 6 am and wait 12 hours for our room and 2+ hours past check in after a redeye.
We prefer a better spot (CBR Aruba or Jamaica) over first available, but also didn't want to suffer lol

Then you really need to decide what is more important, location or how early you can get in to your room.

No one here can tell you what time you will get a room at. Rooms roll over for that day at 6 am, and some people may get their room(s) early, but some guests have to wait until past check in time.

You could book a room for the night before, to guarantee you will have a room. Some guests do that.
 
We prefer a better spot (CBR Aruba or Jamaica) over first available, but also didn't want to suffer lol
1) You might have to accept one and not the other.
2) Requests are exactly that, and are never, ever guaranteed.
Maybe so, but we have never waited 2.5 hours past check in time for a room at any other hotel including Disney properties.
Everybody experiences things they never experienced before, until that thing happens. I never had luggage misdirected - until I did. I never had a flight delayed after boarding, until I did. I never had a flight cancelled at a connecting airport, until I did.

I never checked into a hotel at 4 AM the next day, until I did. I never locked the keys in a rental car, until...you get the point.
 












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