Wanted to jump in here to answer a few points in your post.
- I’ll be paying an annual fee if I want support (albeit I don’t have support for RW8 now);
Yes you do, we don’t limit our support for RapidWeaver, so you still have support for RW8. We are no longer updating that version, but if you have a question or are experiencing an issues with it let us know and we will support you.
Also RapidWeaver Classic’s annual fee is for a 1 year period of app updates. We don’t limit support after that 1 year period has expired, so you can request support anytime needed.
- I’ll be able to use it on one Mac as opposed to the two I use it on now.
With the current Black Friday promotion, I believe the RWC Studio license (2 Macs) is cheaper than the older RW8 license used to be (both new and upgrade versions), so you could pick that one up if you need to use RWC on 2 Macs. Yes the older RW8 license allowed activation on 3 Macs, however if you are only using 2 Macs then that extra activation doesn’t really offer additional benefit.
On the other hand I worry that I’m eventually going to get stuck in some sort of limbo on an outdated version and need to keep current.
At some point that will be true. It isn’t now, but as Apple continues to update macOS, there will be a point where RW8 will stop working as Apple will push out some update that breaks it.
RapidWeaver Classic is the most current version and the one we are still updating to make sure it works on Apple’s latest macOS version.
I’ve identified what seems to be a decent Stack for online payments which is compatible with RW8 and my hosting package can accommodate it, so is it worth it? Are there actually any real-world benefits or additional features available after moving to 9?
The “is it worth it” question is subjective. We’ve pushed out one major release and a ton of patch releases for RWC which include new features, enhancements, and fixes that aren’t present in RW8. A majority of users over on our community feel the upgrade is worth it. A vocal minority on this community feel otherwise.
We offer a 14 day money back guarantee so perhaps the best way of answering your question is to try out RW Classic during that money back guarantee period to see how you like it. If you feel RW8 is still sufficiently meeting your needs after trying out RWC, no problem, you can request a refund. If you decide you like RWC, that’s great, we’re happy you like it. :)
Hope that helps, if you have any questions for us feel free to reach us on our official channels.