We continue to be in the dark as to when the 2020-21 season will start and what exactly it will look like. Elliotte Friedman posted a thread on Friday on what is known and what is still being worked on.
For what it's worth, the NBA is targeting a pre-Christmas (December 22) start date with a 70-game season, so that might be a model the NHL considers as well, although I doubt it'll be a full 82-game season at this point. One major hurdle is the Canada/US border situation, which is why separate Canadian/US divisions might be a necessity (at least to start). Another major consideration is whether fans will be allowed, as the bubble doesn't look like it will happen in 2020-21 for financial reasons. And of course, there's the damned virus, which is showing no signs of slowing down and is in fact picking up in many places.
I won't delve into what might happen any further, but all of this makes it difficult to plan a fantasy season start. The only comparable we know of is a lockout, where drafts likely had to occur (or reoccur) right before the season start. If you have to know soon, I'd say pencil in a December draft on your calendar, assuming they can pull off a January 1 start. December can be an exceptionally busy month with the normal routine plus holiday shopping and activities, which would make for an unusual dynamic if you're also trying to put together a draft that is as close to the start of the season as possible.
Better yet, consider an asynchronous draft via email chain, forum, or Google Docs to pass what's going to be another long dead period. I use this in my keeper league every season, only this season we will be starting sometime in November instead of in August. Slow drafts might not be as exciting as the live drafts, but many of you will appreciate the fact that you'll be able to make less panicked choices.