If your intent is to push product updates down, there is one coming in late January or so if that makes any difference as to timing.  The January PU will be important going forward if use or plan to use the 1099 functionality in the product.

Just a thought ...

Ah so that will be part of the monthly update?  I wondered if that was a separate install just for 1099 stuff.  But yea maybe i do wait then.  But still would like to hear how people push the monthly updates to their users.

It is both,  If the tax year requires changes (2019 did not, but 2020 does due to the reintroduction of the 1980's era NEC form and the reorg of many of the 1099-MISC boxes), Sage provides a stand-alone install in December of that tax year, and the inclusion of that stand-alone in the following product update, which is commonly in January following that stand-alone update.  The stand-alone is generally used by most 1099 users as the January PU does not usually ship until near the end of the month.  

For 1099 usage it is recommended that for year-to-year processing, a single client should be used for that purpose due to the way Sage integrates with the third party 1099 service, so the only client really needed a stand-alone update should be a single machine.  It is possible that this will lead to other client machines not being able to do what the stand-alone machine can do, but with the possible exception of the entry of 1099 beginning balance imports it should not make much of a difference.

Perhaps a reseller or larger company can explain what they do in what I assume is a traditional client-server setup and not a terminal server environment.