Hi Matthew, thanks for the reply and advice!
The MPL-2.0 is not quite as permissive as Rails' (MIT) and is closer to LGPL in permissiveness. That's actually what has me worried about trying to use it.
I've thought about the axes you mentioned. The relevant axis for me is the modififications one. I'd like people to do whatever they want with the software but if they benefit from non-private-use of improvements, then I would like to have access to those improvements.
Best I can tell, researching this, none of the popular open-source licenses really give me this in a practical sense for this type of project. AGPLv3 seems to have the broadest terms that trigger sharing-back but seems more restrictive on use than I want. MPL-2.0 is close but its definition of distribution doesn't include the typical use-cases of this type of software (accessed over a server instead of offered to the user.)
Another thought... I don't think there's much incentive to horde your own improvements to a project like Sinatra or Rails . It's usually less hassle for me to just upstream those improvements than maintain a fork. So a license that requires sharing back might not really increase the amount of code shared back in this type of project over not having an explicit requirement.
So, MPL-2.0 is closest to what I want but probably wouldn't actually impact behavior differently than MIT would for the reasons mentioned. So the risk of picking an unusual license for this ecosystem I suppose isn't worth it in this case and I'm leaning towards just using MIT again and stopping overthinking it and getting back to hacking.
Cheers!