In the grand scheme of things, if you have a 4, 5, 6 day or longer pass, it makes sense to me to head to a park on your first day. Of course it all has to make sense logistically and time wise. If you land into MCO later in the day and the parks close early, then of course, take it easy and maybe hit up Disney Spring your first day. In my case, we landed and were at our resort by 230 and into the park by 4pm and MK didn't close until midnight. It didn't cost of much more to have that extra day in the parks and we love seeing the castle on day one of our trip. We hit up a few fast passes, ate some dinner and watched some fireworks.
Yea, its a totally optional thing. I now days upright refuse mid day arrivals. Its either i'm at my destination before nine or ten am, or i'm there after six pm. That obviously allows for nearly 3/4 of a day to go on with your plans, or an evening to relax and get started early the next day depending on where we are going and what we are doing. Back when we'd arrive places mid day, it was hard to figure out how to burn up a partial afternoon and evening, ontop of depending on where we go, sometimes its a haul and we are tired, or if either of use worked that morning, etc.
So breaking it down, yes, a four or six day pass are reasonably priced. Lets take a look at the six day simply because its the cheapest. A family of four, would pay approx 70 each, that's 280, for approx eight hours. if you can arrive by 4pm with a late close at midnight, honestly not too horrible, if you can work some fast pass magic (aka book another headline ride immediately after you use your first, if you can even do that anymore), hit two headliners and sneak on two or three other rides with fairly short times (eyeball the app for wait times every so often, you always get lucky with something). I'd be okay with that. Anything less, probably not.
In big bold letters, all the above is purely speculation, and totally a personal preference, and one personal preference is not better than another. *disclaimer for folks not good at interneting ;P.
Yes this could be a whole new topic. I'll stop thread hijacking. But i'm actually curious at what point people will say a partial day is not worth it.
Back to the main thread. The MK express, you don't need to pick up your bags, but don't expect them to be in your room when you arrive on occasion, they come off the plane along with everyone elses, and get sorted out near the end. But if you are on the MK express, you bypass having to wait on them (gawd the dreaded wait at MCO, i swear i get it every other time, even on different airlines).
Again with the 528 and 4. Whether you are on a MK express, or in an uber, you still have to contend with that cluster. Our evening pick ups we hit traffic maybe a third of the time. If everything goes well with luggage, and your on the road by say 7:00pm, your still on the edge of some traffic. Anywhere from 15 to 20 minute delay, to 30-45 minutes. Totally random, but the entire way through that rush hour can be hit or miss. 4 always seem to have accident delays also. NOT saying it will be bad, we have had numerous pleasant trips down those two highways, but have run into some junk on those roads a handful of times. Just something to consider.
If your dead set on it, I would at least have a plan B in this case. Any one aforementioned thing could add another hour to your arrival at the hotel.