> The selling company needs to know if its worth the effort
It's not worth the effort.
It's killing your ability to scale your sales process. Unique adaptations kill your ability to scale product development, as now you have a bunch of one off deployments. Figure out ahead of time what discounts you want for various tiers of user count.
If you are a startup, avoiding things that don't let you scale are critical.
This is what I meant in my comment. The seller needs to know what the buyer wants, maybe its a big bulk discount or an extra feature. If the seller decides the discount is too steep, or the extra feature doesn't fit with the road map, then no deal. Or maybe the deal really is that big, and it's worth catering to some one-off demands.
None of this means "hiding" information, but you can't put something like "We'll do X hrs of extra work if you buy Y licenses". Just like the any store might have a 10% discount if you buy a dozen, but if you want 50,000 then there will probably be a conversation involved.
Nah, what you do is you add this feature for everyone, unless it doesn't make sense