Zarloff, you shouldn’t have to “learn a lesson.” Whoever is responsible for implementing the licensing mechanism for the warehouse should be handed a mop and told that they have a new career. This wreaks of an unexperienced intern writing critical code, or simply a feature that was implemented temporarily that has never been revisited and properly patched or implemented.
I’m not starting a new thread because this is my exact same topic, so I’m adding to it.
There are several user scenarios that have simply not been thought through, or that have been ignored. The lack of handling of these scenarios has prevented me from activating some plugins when needed, at odd hours when your tech support isn’t available, and it has even prevented me from repurchasing plugins to work around the issue. I know many people gripe about spending $1 on something, but some of us buy tools that we need and the plugins at even $100-a-pop are insignificant to the productivity that we get from them. So in my case, sadly, I can’t even support the developers by purchasing additional licenses to get me going in a pinch. If I registered as a developer and put my own custom code in the Extension Warehouse for a price and my users ran into these issues, I’d be seriously pissed off.
On the Mac version, I have several extensions for which the number of activations cannot be decremented. A typical app install on the Mac is to throw the outdated app or its enclosing folder in the trash and drag the new one to the Applications folder. It’s been this way for years and will continue to be this way for many many apps for years to come, so the developers should be aware of this and handle this scenario in their warehouse implementation. However, I’ll acknowledge that SketchUp is doing it their new way, I didn’t read all the docs, and I need to deal with the new way of life. The problem is, I have no accessible mechanism to deactivate all my previous activations and start fresh. I also have no reliable way to deactivate old plugins one-by-one to at least free-up an activation for reuse. I emailed support a few days ago, I got a response that someone had to add activations because they couldn’t deactivate any, they added a few activations to some of my purchases, and this got me going again with one of my most used plugins. I thank them for that help, but oddly, they suggested that I post in the forum about this issue. Isn’t that tech support’s job to convey this info up the chain?
Back to the issue… I have reinstalled 2019 and 2020, dragged copies of the extensions from the old plugins folder to the new plugins folder, made sure I’m signed into the warehouse, checked “My Downloads” in the warehouse to observe my activations, and tried to uninstall the appropriate extensions, but it doesn’t reliably work. I have managed to decrement the activation count of one plugin, but I usually get a silent uninstall with an occasional Ruby console error of “Extension returned wrong type for method mark_as_uninstalled” that points to at least one underlying issue. So, my only choice is to email support, wait for them to work-around the underlying issue if they’re able and willing, and prepare to deal with the issue again in the next SketchUp update. Wonderful 
I was willing to repurchase the immediately needed plug-in, but I wasn’t able to. The warehouse button would let me “Install”, but all it did was to install a fresh copy, complain that I wasn’t licensed, take me back to the warehouse to buy a copy, which of course only offered to let me install it again. I mean, WTF? Again, as a developer, I’d be pissed. As a user willing to spend $, I’m pissed.
So I’ve wasted way more time that I should have to because relevant developers didn’t actually think through all the user scenarios, and this has left me incredibly frustrated during times that I could not get immediate help. I’m not saying I’m jumping ship or any of that cr_p because SketchUp is awesome and I rely on it daily. I love it. I’ve been a user since it started life as AtLast in Colorado, and will be until yet another company buys it, runs it into the ground, and the core developers leave and start yet a new company with something better
but for the love of god, listen to the users who have issues and re-think how you’re implementing the extension licensing.