The thing is we usually check out about 7am because we need to get on the road. And there are never any housekeeping staff around. I don’t think they start until 11 at most resorts.
Housekeeping cms are usually in the hallways by about 9am at Boardwalk Villas. Can't really speak for other WDW resorts as I haven't paid much attention.
Often I've been on split stays or switching room types. This is over 25 years of owning and 1st DVC visit in 1997.
In the earlier days I've had a few times where I didn't get my room until after 4pm. That was almost consistent at AKV unless staying concierge level. I had one particularly late at BWV where it was about 9pm. I didn't arrive until after 8pm and that was before our ability to indicate arrival time and before we got room ready texts.
I've had one instance where I arrived near 4 at BCV got room ready about the same time and couldn't get in the room until 5 because the door wouldn't open. Bad battery was the cause but it took forever to get this resolved. Once maintenance were called, they had it fixed in minutes, but the runaround was the desk - go back and try this key, assuming my magic band was the problem. I had already tried phone and band, plus an in the hall cm had tried as well. So direct to room was a farce. I accepted a small compensation on this, offered not requested as I was soooo frustrated.
Another time at BCV before texts I was left to sit for an hour past the time the room was ready, when a different CM says, 'oh, that room was ready at 3:05'. Had arrived at 3, room not ready, checked back at 3:30, 'not ready', after 4, new CM.
A couple of times I've waited longer to get my choice of area.
And when it was all important, on Feb 23, 2025, I got a 2 bedroom BW view at 1:31pm. My guests were out shopping for important stuff like wine, beer and snacks plus assorted breakfast items and fruit and cheese. They got back about 2ish and straight to the room! BWV made me look so good as their host!