Are you saying I let them use it for free, iron stuff out, and then ask them to pay to continue using the service?
I expect issues. The service has a pretty long, horizontal and vertical series of steps to complete. I don't know if I can make them pay what I expect and have them experience something awful.
Nope, actually do everything to get the first few to pay. Once you do that, you can at least be certain that there are people willing to pay for your service/product. You can focus on growing your customer base after your paying customers give you great feedback.
Seems like a bold move. I feel like if I tried doing that, I'd get requests for refunds and a lot of bad press. But I guess your point is that at least I'd have to learn why, and then fix that for my next trial.
Why do you think it is a bold move? Since you have a handful of customers in the beginning, things can never get out of control. Even if your customers don't like the service/product, you can still do something about it - you cannot do it if there are hundreds.
I expect issues. The service has a pretty long, horizontal and vertical series of steps to complete. I don't know if I can make them pay what I expect and have them experience something awful.