[sampsonitify]

There are no rules to life - you get to decide what you do with your own life. Assuming you make a comfortable living out of what you do, the Craigslist approach - they make a LOT of money but leave 90%+ of what is possible on the table - is a perfectly valid plan.

If you want to make more - and the reasons for that can vary from pure greed to absolute need - experimenting with pricing can have the best effect, as every extra dollar MRR compounds over time, and it is often easier to get 10% out of customers than 10% more customers. The patio11 "charge more" advice is an easy place to start, and if you grandfather in all old accounts, there is minimal risk in doing so.

But it is your business, so do what you think is best.