I'm not from Roll20, but the likely reason they limit it to five games is two-fold: 1.) licensing restrictions, 2.) promote sales. Whatever the specifics regarding the contract between WotC and Roll20, I am sure one or more of the rules that governs the agreement requires that Roll20 prevents users from pirating material. If one person could purchase all of the books and then share those books freely with all of their friends, then why would their friends purchase the books as well? This all boils down to the fact that both WotC and Roll20 want to sell as many copies of the books as possible to generate sales. The five games/fifteen players metric that they came up with was likely a compromise. Advertising that you can share your purchased books with five games and up to fifteen players is an attractive proposition to customers of Roll20, many who started from the position of "I already have the physical copies of these books, why would I buy them again?" All in all, I would agree with your suggestion that Roll20 should provide the ability for users to increase the number of games and players with who they can share their material. I would guess though it would require users purchasing additional copies of each book to remain compliant with the agreement with Wotc. For example, if purchasing the PHB once allows you to share it to five games and up to fifteen players, if you purchased a second copy of the PHB, you could share it to ten games and thirty players. -Adam