In general, I advice people to get a perpetual when they are not into “modern” stuff (Viewers, Collaboration no need to get involved in bigger organisations) They can choose whether or not if the new versions are worth the upgrade and pay the Maintenance if so.
We have customers still using v8, for that matter, if it works, it works.
I advice others who are into modern things (VR-AR, Webservices, Larger companies, Data exchange, Trimble Connect) to go Subscription.
Still, there is some misunderstanding about licenses, though. You buy the right to use it and are permitted, if you want to own software, you can create or built your own.
So you have to decide if it’s worth paying to keep on using the ‘latest and greatest’ or keep stuck with the version ‘as is’
As you have noticed, the maintenance for network licenses doubled around februari, last year. They too have to decide to keep using the version they have, or upgrade to the newer. Prices for Maintenance of a network license is more then a Pro Subscription. I do not work for Trimble or SketchUp, so I do not know what future plans they have for the Maintenence plan for Stand Alone licenses. It is not going to be cheaper, for sure.
It is part of the (n)everending story: in the end, Trimble’s stakeholders will decide, I guess.