To justify prices in the > $2k region I think I would need to add some sort of interactive component (webinar or what have you), and I have no time on the schedule for that in the next couple of months, so I went with something which was totally self-guided for my first try. I might revisit that eventually, if there's lots of demand for it and if it makes sense for the business.
You want 2k+? -- offer to edit 3 emails -- you probably wouldn't get enough takers to take too much time. Also, it price anchors the $249 and you can do it like Kickstarter and limit the # of sales of bonuses like this.
For $10k or more, write a first draft of emails and look over the final draft after they edit.
Buying is a trivial decision at $300. We sell a $350 product, with high margins. A single sale and this course pays for itself. (2-3, if you include my time spent watching and implementing it)
edit: turns out I didn't even notice the price. It's actually $250. I was prepared to pay anything up to $400 without thinking about it or discussing reimbursement with my company.