Are there plans to release anymore software updates beyond November 4 to cover the remaining year of M&S? I’m trying to figure out whether I should even pay for another year of M&S if there are no planned software updates after November 4, since that is the only reason I shell out for M&S. An official response from Trimble would be appreciated.
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"We are a publicly traded company, so we cannot provide any detail or info on future releases or release dates.
If you are under maintenance and support when a new version is released, like 2021, then you would automatically get that. If you don’t have maintenance and support or your subscription has lapsed, you would not have access to that."
Direct response from SketchUp support. I don’t see why being publicly traded has any bearing on software update schedules 
They say it means they can’t release info on future releases, it doesn’t say it has any bearing on the schedule.
so Trimble should be able to say something like yes, there is a planned update before xx.xx.2021
I expect they’d tell you there is a planned release before 31 December, 2021.
There isn’t any reason to even waste time asking about when they will release SketchUp 2021. It’ll be released when it is ready to be released.
That’s info.
I think what Trimble has said is that in the future new features will be introduced more incrementally than in the traditional yearly update cycle. As far as I have noticed, they already have started working in this manner, with new features introduced in “maintenance” releases.
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Basically, hang on to the classic license and gamble that maintenance release during the last year of maintenance & support and will be available to perpetual license users.
Classic maintenance and support can be renewed up until November 4th. It still is for 12 months, which means that you get any updates until that time runs out. If release dates are anything like they have been in the past, that would mean you would get the upgrade to 2021 when it’s ready, and you can bet that nobody will be entitled to a Classic upgrade to 2022.