A couple of thoughts based on our similar experiences, some for your benefit, some for other readers.
- treat the report upgrade pricing as if it was a sort of insurance quote. You know some will be low, and some high, but you win overall. Even so, it makes sense to approach the report complexity in a low/med/high context. We had good look with presenting their list of reports to them grouped by h/m/l complexity, and quoted a total for the bunch. We then told them that the price would come down more by removing an H report than a L report, but we never defined the per-report price for any because ""the mix actually defines our cost.""
- Remember how Kless preaches to handle discounts. Just because he customer removes 1/3 of the items during negotiation, there is no reason for you to reduce the price by 1/3. Your offer with high for the 1st, and lower for the next ones is similar to that approach. In nearly any tech work, the actual technical tinkering is half or less of the total time spent on the project.
- If you can structure the proposal in 3-levels you can beat the the price shopping. The base level might be really cheap, but you could take 2 weeks to convert them after the upgrade, with customer review required within 2 days of each release or they take it as is. The higher level is tied with a sandbox testing and training step, and they get more flex in responses.
- We also get good mileage out the 3-level approach to upgrades with complex parts that could be easily shopped by mixing the report upgrade options with the other combinations of enhanced deliverables, responsiveness and flexibility so they can't really pull them apart from each other.
It might not appropriate for this customer because it's so erratic, and it might not be appropriate for all your upgrade work. But for these where parts of the problem are competitive pricing, I've found creative use of the 3-level proposal completely removes the problem. The anchor price is low enough to be not obviously higher than competitors, and customers tend to focus on choosing between the 3 offers rather than on whether your offer is too high competitively. That part is really remarkable. I think we've had only 1 upgrade at the base price in the last 18 months.
Have you thought about adding something to your pricing about multiple quoting for the same upgrade base? In other words, the first quote from v4.1 is free. But the next one will take $500 evaluation fee, with half applied to the eventual upgrade. We don't do it, but our small base doesn't tend to generate the quantity of frivolous upgrade requests that yours apparently does.