First of all this satisfies the criteria of "offering options which are win/win" because the current environment is this: The Covid situation is having an overall harmful effect on Trump's re election chances. And this has largely been dictated by the left and the media.
Option 1 is that they allow for delay of the election which helps Trump because A) he gets longer in government and B) he allows the Covid situation to change to his benefit, thus removing its negative effect on his re election.
Option 2 is that they fight to have the elections now, and are forced to claim that the covid situation isn't that bad, which again helps Trump.
And beyond this, from a strategic level, everyone is about to fucking lose their mind. Based on a single tweet where he's musing about a plan, everyone is playing their best hands in response.
Art of the Deal.
The argument from the left is still going to be that we should hold elections on Nov 3 with exclusively mail-in ballots for public health and safety. I honestly don't see how Trump's tweet changes that particular argument. If you believe in the left's argument, you could just say "no reason to delay if we do mail-in ballots." I think it's more likely he's deflecting/distracting from something else going on behind the scenes and he wants this tweet to be the focus of the news cycle for the next couple of days.