Roll20 is a fantastic tool... but there could be many improvements that could be done to it both in terms of features or ergonomics. Why not bite the bullet, do a kickstarter, raise some money and hire the developpers required to bring those feature to the game ? Given the popularity of Roll20, a crowdfunding campaign is a near guaranteed success. Please, take my money. Just do it.
You hav e my vote on that!! I would gladly contribute to that evolution of roll20. There are a million and one things thats are great about roll20, and there are a million and one ways to improve it. I would start with a nice visual inventory manager like any of your typical RPGs out there now...
I am new to Roll20 and at the same time I'm excited for all it has to offer and disappointed for what it could be. There are so many good suggestions, many of them many years old, and so many enhancements that could take the platform to the next level. I don't know if they have financial problems or lack of organization, but if you look into DnDBeyond, by Curse, a much bigger company they are doing an amazing job, there are forum Mods who keep an eye at the community (through their own forums) The truth is that Roll20 is an amazing tool, but if it doesn't improve in a couple years, it'll loose a lot of ground to DnDBeyond and alternatives.
I'd love to see roll20 up development to the next level. Suggestion for high tier reward could be like $300 for a permanent pro account (first 1000 backers) boom, instant 300k dollars on top of the lower tier backers to go towards kicking things up a notch. I just want this thing to reach its potential, I've already invested like $500+ in to marketplace content and subscription fees because you're the best, but new features seem to come out slow and half working. I just want roll20 to be the best it can be.