Problem A is a way better problem to have. Of course, no business would intentionally try to cultivate a user base of picky, high maintenance pain-in-the-necks. Nor would it be anyone's long term goal to be hacking on user requested features. But if those things bring users, easy trade. It's hard to think of any problem that would be more important than the problem of not having users.
There's also a difference between holding your customer's hand and building unsustainable expectations. The only expectation you've built by holding their hand through the onboarding process is that you care about your customers and want them to have a great experience. That's exactly the expectation you want your customers to have. Many startups have been incredibly successful at acquiring customers from incumbent businesses with more features and possibly cheaper products, by simply caring more about people.
At the end of the day there are people using your product (presumably). The more those people feel you care about them and their problems, the more likely they are to give you a little space as your business gets off the ground. Maybe they're willing to tolerate a few minutes of downtime, the occasional bug, or missing feature, because they know that they're always going to be treated well by your team.
Cultivating strong customer relationships is a great element in any business, and it's virtually a requirement in modern B2B.
A) Having users, with high expectations
B) Not having users
Problem A is a way better problem to have. Of course, no business would intentionally try to cultivate a user base of picky, high maintenance pain-in-the-necks. Nor would it be anyone's long term goal to be hacking on user requested features. But if those things bring users, easy trade. It's hard to think of any problem that would be more important than the problem of not having users.