Looking to figure out dates for 2021:
We would either go Wednesday June 2nd-11th or Wednesday October 7th-16th. We went the week before Columbus Day in 2019 and it rained the entire time(honestly didn’t mind at all) but the schools here have changed their fall break to where we only have 1 week to choose from instead of 2. We are large fans of entering the parks early leaving around lunch time and coming back in the evening. Is June extremely hot?
We’ve been twice in early June and once in early October. Yes, it was extremely hot in June but it wasn’t a problem because we expected it. We had rain every day both times of the year BUT October is in hurricane season and we were lucky enough to leave just before the parks had to close for a hurricane. Not something you have to worry about in June. 
We went the 2nd week of October 2019 and it was beautiful, picture perfect weather every day! We are planning our next trip for October 2021 and can’t wait.
How about the crowds? Are the relatively the same? We are hoping to rent DVC points and the cost is the same-we have been in October twice and done MNSSHP twice as well. Just wondering is June may be better for us in 2021 due to the 50th Anniversary as well. My husband just tells me to do what I want so I need input from others!!! THANKS!
If you can do October, I would do that since June is summer vacation season.
We would have to do the week of Columbus Day in October-for June we would be doing the very first week of June. I know October has been getting busier every year with more schools taking extended Fall Breaks-I was thinking early June hoping some would still be in school
I have been in June at that time twice. Crowds are heavy- one year it was especially heavy and we had 8-10 crowd levels the entire week.
I think you need to also consider what this year has brought us in terms of Disney shutting down. There is talk of Disney opening back up in the middle to end of May, (DIS members particularly) but that could always be pushed back to June 1st. Regardless, if you plan to go the June 2nd option, consider that Disney might not be back to 100% what it usually is. It could take a few weeks to get all their staff back, they might phase-in food location openings, etc. Also, you cannot guarantee what the crowds will be like the beginning of June, as the crowd calendar is partially based on historical data and Disney has never been closed this long. Some fans might rush back the first chance they get, while others might not yet feel comfortable going to a crowded place so soon after the virus eased. (Assuming that is the case.)
I think by October everything should be back to the norm, so it might match your expectations when you think of “typical Disney” and all the connotations associated with that.
Both have their pros and cons, but I wanted to point out some considerations when it came to the June date.
I don’t plan to go until 2021 
Ahh gotcha! Nevermind then! 