dmure -- Just don't overbook your time and stress out when it doesn't work.
Whenever we flew into MCO, we were always right on target with getting in the room approx 1.5 hours after landing. And that was with a towncar.
I would say you might be done checking in at 1:30.
Ae you driving? If not, it will take longer to reach DTD by WDW bus.
I would say you will be doing good to be at DQ at 2:00.
And if taking WDW bus service, again allow LOTS of time to get where you need after DQ. Possibly 1.5 hours.
I don't think the buses go to the west side -- and haven't in years. But I could be wrong on that.
If time is a factor, even a taxi may be better for you if you are not driving.
Again, your timing will depend on if you are driving.
Also, is DQ allowed with a feature? Or are you having to pay for that half day?
Depending on how late you stay up, DQ offers a late evening entry at a discounted price. I never paid much attention, but I THINK it was $16 pp from 9 p.m. on.