Yes, as Tore already explained, this strategy has already been successfully used for registering .no domains beyond the registry imposed limit.

Registering a .no domain costs merely 20€ or so, and until this year, there was a cap at 20 registrations per organization.

Feel free to ask the owners of Domene Klubben 1 through 442 if the inconvenience of registering 441 extra organizations was too much, even with all the manual paperwork needed back when they formed in 2000.

In the case of IP addresses, the cost savings are significant enough that the bother of registering a few hundred extra organizations shouldn't be too bad.