I just spoke with @pradyunsg about the timing of the 20.3 release. Conclusion: @pradyunsg and I are leaning towards modifying the plans for 20.3 to:

a pre-release this week
a stable release in mid-November, around Nov. 11-12

Reasons: In terms of features and showstoppers, we are set to be ready to release this week. However, a few things have come up, just now, at the end of the 20.2 beta period:

New resolver: Build automated testing to check for acceptable performance #8664 (comment) We need to nail down our policy and implementation re: Python 2 support.
Azure macOS job is failing + "pip search" throttling #9030 and Add rate limiting to the XMLRPC Api pypi/warehouse#4321 (comment) We've just run into some CI blips/glitches that have gotten in our way and are not yet completely resolved.
As Election Day in the United States (Tuesday, 3 November) approaches, we're seeing an increasing risk of civil unrest in the US (which may occur approaching, on, and immediately following 3 November), and we're considering the risk that a disruptive change to pip, released only a week or less before the election, would make it harder for civic tech developers/administrators and data scientists to use Python (in tools to assess/counter voting suppression and violence).

We planned an October release, in accordance with the usual release cadence, before the full scope of the pandemic and the US election situation emerged. But, as the release policy states,

The release manager may, at their discretion, choose whether or not there will be a pre-release period for a release, and if there is may extend that period into the next month if needed.

@pypa/pip-committers heads-up in case you are inclined to agree or disagree.