All accounts on web connect show waiting while doing one step update

If you haven't done so already, I'd say it's time to call Quicken Support on the phone and request help.  Let them do a screen share session with you to review a download log file on your computer, to determine the nature of the problem and to figure out how to fix it.

Quicken Support:

• To contact Quicken Support, please use this link only:
  https://www.quicken.com/support#contact-support  and select Chat or Phone support.
  Support is only available during posted hours of operation
• The phone number to call can be found at the support website.
• To start Chat or see the support phone number, your browser must allow popup windows from https://www.quicken.com
  See https://community.quicken.com/discussion/7870684/faq-talk-to-support-does-not-respond#latest
• If you are eligible for Premium Support (purchased separately or included as part of your subscription to Quicken 2018+ Premier or HB&R) call the number that can be found at the top of your My Account page at https://www.quicken.com/my-account  (US) or https://www.quicken.com/canada/my-account (Canada) next to "Quicken Premium Support"  when you log in with your Quicken ID.
• Other links or phone numbers found elsewhere on the Internet, even in some posts or emails received from other Community members, may not be from Quicken or may not be up-to-date. Use those at your own risk.
• Unlike other so-called "Quicken support providers", the real Quicken Support is free for all currently supported versions.