I definitely follow the line of reasoning there, Faruk, but I don’t think that’s quite how it breaks down.
Any license is intended for a single owner. As far as WooCommerce is concerned, that’s their biggest concern. Why? Because support largely scales on a per person rather than per site basis. So if I have a license that I use on 25 sites, I’ll most likely handle a lot fo the needs and then be a single voice when reaching out to WooCommerce for support. Since that is the case, it’s feasible for them to give many sites for slightly more, as the cost of support isn’t really going to increase much for more sites. There’s also the good chance that buying in bulk means it’s an agency (or professional at least) which means less hand holding.
I’m not really speaking into your question about divvying out a bulk license, but I wanted to shed some light on the economics behind licensing. It has more to do with the practicality of cost than sales tactics.
To be clear, my agency does manage plugins for a lot of clients, so we have many of these plugins in bulk. We share some of that savings with the clients, but handle a lot of support that would otherwise fall on WooCommerce.
Hope this helps.