It very much depends on the problem domain, but 2,3 and 4 are the real dangers. The solution to 2 and 3, for me, is to repeat this every time I'm dealing with

It very much depends on the problem domain, but 2,3 and 4 are the real dangers. The solution to 2 and 3, for me, is to repeat this every time I'm dealing with a potential client : do they value their time more than their money? People who value their time are quite willing to commit money to save it / use it better. The solution for 4 is way wrong. You never ask people how much would they pay for things, because the answers are always wrong. You price things high and bring down the price until you're making sales and about 5% or so of your customers are complaining about the price. That's as close as you'll get to a scientific pricing strategy. I asked a couple of customers how much they'd pay for a new software product I was writing. They all low-balled the figure. In the end I priced it 5 times what the highest suggestion was, and it has sold well. If I had been receiving 5x less revenue, I would have given up before the product took off.