After talking to DH I think we're going to hold onto our Dec 2020 ressie until we see how things play out into September ... but I think at that point we may reschedule to 2021. We won't go for a highly reduced experience... no fireworks, shows, tours, restaurants, parties, CP, etc... are not an option as these are part of what we want to enjoy and we'll defer if they aren't going to be offered.
To some extent (and I know this sounds selfish) but if you're paying $15000 -20000 for a 10 to 12 day vacation (between flights YOW to MCO return, hotels, local and onsite parking, transfers, kennels, tickets, car rental, events, etc...) it's a lot to spend for a limited experience.
I suspect buying medical insurance for travel to the US (for Canadians) will NOT be cheap going forward --- but will still be important to have. We won' t go to the US without
travel insurance in place (Trip cancellation isn't a thing at all for us since we do room only and buy modifiable flights, etc...)
For us the quarantine period will be a thing since we have a DS who is in high school -- the number of quarantine days (14 arriving in FL and 14 on return to Canada) plus vacation means summer is the only option and I'm not so sure we want to spend time in FL when it's super hot. There's no time but summer that can accomodate 2 @ 14 day quarantines (1 in FL, 1 in Canada) - plus the actual number of days of the trip.
If the quarantine thing is resolved we'll rebook to Christmas 2021 in a heartbeat. (This one is best case for us -- and well... assuming quarantine isn't req'd means things are more stable -- which is good for everyone) but means we lose our bounceback and the discount for the CDN tickets since they were only good until the end of 2020 (unless they extend them) which could make a summer trip more attractive depending on the situation.
I guess the main thing is --- we want to go to WDW when we feel the situation is under control but there's a lot of things in play at this point and have no sense when things will change enough (safely) in the near term.