It's interesting, Gitlab is one of the products I most want my organisation to pay for but am constantly defeated by their pricing plans. It sort of maps onto this decision because what I consistently found was that Bronze offered almost no value in terms of features but the step up to Silver was so big that there was no way we could dive in at that level. So we just lived on the free tier and by and large get by wit…
If there was a way to assign licenses to groups or individual users in the self-hosted version we would be paying for it already.
Same as you I really want Gitlab to do well, but the lack of options with licensing makes it difficult to adopt. A lot of other enterprise software allows for per-user license assignment like Office 365, Salesforce, Jira, etc...