Thinking even more on this (as if we want to get this off the ground we need to make it as monetarily appealing to Roll20 as possible), what about this. The current price for a Plus Subscription is $50 for the year and you get 3GB of storage (plus a few other fancy benefits/features). What if you added a subscription tier below that called " Extra ", for example? The only difference between the Base and Extra subscription is the storage limit, nothing else changes. The Extra subscription gives you 1.5GB of storage for the annual price of $20, let's say. Now on top of this, Roll20 could introduce a storage upgrade purchase that users could buy, however instead of it being a one-time purchase, it just adds on to your annual/monthly fee. This way Roll20 can continually earn money off this instead of it being just a once-off payment (making it more appealing for them to implement). I have no idea about prices but as an example you could pay an extra $5 per year for an increase of 1GB in storage , or an extra $10 per year for an increase of 3GB in storage , and then maybe one big one of an extra $15 per year for an increase of 5GB in storage . This way users can purchase as much, or as little, extra storage as they wish and Roll20 can continually make money of them each year. Plus, just like a regular subscription, if users decide they don't need that extra storage anymore they can choose to cancel it and go back to the base storage of whatever subscription tier they're in. I feel this would please users and also be a great money-making opportunity for Roll20 :-)