I guess the one thing I've realized is the problem with this is the one more feature trap. Sometimes those people who like your toy will never pay for it, which may be fine depending on your goals, but the issue is there just as relentlessly demanding as paying customers. It's demoralizing to have a side-hobby project which you don't want to monetize but still has all the demands from "adopters/customers" that a paid solution would. It just destroys your passion for that project because it ultimately it just becomes work.
Really charging for a product is great and I think hacker culture seems to dismiss it because its not in the ethos but if there's anything in retrospect I think I've learned so far with my many failed side-projects is charging for them is the best way to have a great personal experience and best experience for who your building that product for. Mostly because it aligns incentives appropriately.
As much as I've enjoyed some of my passion projects I can't think of one I ended up "finishing" which I wouldn't get some monetary gain from. Because let's be honest whose passionate about setting up a Jenkins server, or implementing git checks, writing unit tests or creating onboarding documentation for cranky free or OS users? At a certain point a successful side-project/product requires you to do things you wont enjoy doing, and honestly some of those things may be the most important things you do for the "success" of that side-project/product.
I'd rather be spending that time with loved ones, enjoying the sun, which is ultimately far more rewarding than a few git stars or upvotes for ego. With that being said I think if you utilize this approach which is basically just freemium for B2B like projects it could be a powerful step towards finding your ideal customer and getting paid users, but it has to be just that a step towards acquiring paid users.
Just my 2c