But it's not worth $100/mo, or 2% of my gross income, for example. I didn't make so much as a freelancer that i could tolerate either of those financially. And It doesn't remove the need for a CPA, just helps with the ability to pay that taxes you owe.
Not about risk, it's about people putting their hands in my pockets. I can only tolerate so much. I'll pay to solve the problem and make sure they can continue to do so for me, but if it becomes a matter of opportunistic behavior on the company's part, I'll go elsewhere or nowhere instead of being taken advantage of.
And you're absolutely right, we don't remove the need to have a CPA, we DO, however, reduce the time you need to interact with your CPA and make it really easy for them to do their job. Given the hourly rate of my CPA, I've paid for Painless if I can reduce his work by almost an hour. We're finding that CPAs and freelancers alike are really digging what we've built thus far.
All in all, this is a product to help people like us solve the same problems we've run into over the years.
Regardless of mechanics or feature set discussed elsewhere in this thread, selling me on an extra $120/year is an increase of 30% to my hard cost of dealing with taxes per year.
The correct price lies somewhere between $0 and the cost for you (or a CPA, $80-150/h) to do it. A percentage is fine too, as it's essentially risk free for the user (no income = no cost that month).