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The reason you have seen RoboHelp 8 recommended is that version had fundamental changes to the code that particularly affected lists. See Lists in RoboHelp on my site for information about that.
This link lets you download any version of RoboHelp back to and including RoboHelp 8. Download RoboHelp | 2017, 2015, 11, 10, 9, and 8
In theory you can upgrade to the new 2019 from any version and in most cases that will work OK and is the first thing to try. If it works OK, then you're good to go but if it does not, then the next step would be to upgrade to 2019 Classic first and then to the new 2019. In your case it's a bit different because you are going way back in versions and having to cross the RoboHelp 8 upgrade.
In your shoes, I would try going to 2019 first as there's nothing to lose, if it doesn't work, trash it and try the other approaches. You can download any version and provided you have never used it before, it will run in trial mode for 30 days. Note though that many of the older versions are not supported on Windows 10. That doesn't mean they won't work, just that there is no support if they don't. See Versions of Windows and MS Word compatible with RoboHelp for information about that.
The basics of my Lists topic should still hold good.
I would be quite interested to see how well an X5 project upgrades. If you can share the X5 version, see the Contact page on my site and send the project as instructed there. Do make sure you include a link to this thread and please do not email the project direct. I will run the upgrade and let you know.
See www.grainge.org for free RoboHelp and Authoring information.
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