I am currently on Catalina 10.15.7 - what is the next OS upgrade path, Monterey? Any recommendations

Personally, I would go directly to Monterey if your MacBook Pro supports that.

The model year of a MacBook Pro is available at Apple menu > About This Mac.

A mid 2012 through early 2013 MacBook Pro can be upgraded to Catalina 10.15.7 but no later. See: https://support.apple.com/en-us/HT211683

A late 2013 and mid 2014 can be upgraded to the latest  version of Big Sur macOS 11 but no later. See: https://support.apple.com/en-us/HT211683

An early 2015 or later can be upgraded to the current version of Monterey macOS 12. See: https://support.apple.com/en-us/HT212735

ajc497 wrote:

I just added more context in another reply, upgrading my wife’s 2017 MacBook Air from catalina To Monterey

As Neil said and as show in How to upgrade to macOS Monterey - Apple Support make a backup (a good idea even when not upgrading). You shouldn't have any issues going directly to Monterey with a 2017 MacBook Air.

Back up your data, check your applications for compatibility, and if your Mac model is recent enough, click on Big Sur or Monterey. You can upgrade directly.

(210629)

I do recommend macOS Big Sur first big make sure if your Mac can support it if not don’t even can support macOS Monterey