If it were me traveling, I would pick two trips but it’s just a 1 hr and 50 minute plane trip for us. If I were you and flying from Canada, I would do one longer trip.
another vote for longer trip. my family likes to chill a lot, especially when going in summer where the heat encourages us to hide out in the room in the afternoon.
I think my answer to this one would have been different a few years ago. And I think the answer kind of depends on what you hope to accomplish. If you are focused JUST on ride experiences (which has pretty much been the case in our past trips), then doing 2 shorter trips, to me, makes more sense…this is because it is just enough time to get on the rides in all four parks. Then, come back a couple years later to do whatever is new, plus the other rides you love.
But now? I’m leaning toward the longer trip. There are two main reason:
- The dynamic of Disney has changed over the years. In the effort to avoid lines and waits, the battle for Fast Passes has become a necessary evil. And with the tiers, it makes it even worse, because you can only realistically plan on one tier 1 per day, and then wait in a super long line. BUT, if you have a long trip, you can schedule multiple days in the same parks, and obtain a tier 1 each of those days (unless you are staying off property), plus get in bunch of the tier 2s. This frees up time each day to then focus more on things like ADRs and shows, etc.
- As I’ve gotten older, and as I’m planning two trips this year, one “action packed” shorter ride-focused trip, and a second longer relaxed trip with just my wife, I’m finding the appeal of just being able to plan the ADRs, a couple FPs, and then just allow the days to play out how we want means a much more relaxing trip. With the focus/pressure off the rides, we can just “wander aimlessly” (to some extent) and enjoy the journey as much as the destination.
So, I think my vote is for longer trip…at least, maybe 8 days minimum (2 days per park). Our May trip is technically 10 days, 9 days in the parks…but three of those are Universal days, so we have to still kind of squeeze things in. I don’t expect it to be a relaxing trip. 
I already replied once and then rememberd that the 50th anniversary should run from late 2021 through 2022, which could mean less active construction durring 2022? I am under the impression that there are plans or rumors of plans for an awful lot of construction before and after.
I prefer 2 shorter trips. We usually go for 5 nights, but I have been longer a couple times.
This is a good point! If I was doing one longer trip I’d want to wait until Epcot was done and a lot of other construction.
After our April trip we won’t go back for 2-3 years, hopefully when a lot is complete!
My first reaction would be to do the longer trip, BUT with all the new cool stuff, I would be tempted to to the two shorter trips. However, since I was drawing it out, I would talk myself into two 6 day trips 
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