This looks really cool, and I can see where some people might like this.
I'm a firm believer in people running their games how they want to run them. For me, I probably won't use this as I think it might reduce the investment and attention from my players. For a couple of reasons:
1) I expect my players to learn how to use Fantasy Grounds. If, after a couple of sessions, they still don't know how to do something straightforward/common, then I'll do a separate overview session with them. Just like in a face-to-face game, I'd expect my players (in an ongoing game for a system they should be familiar with) to keep their character sheet accurate and up-to-date and know where to find on their sheet the information they need to play.
2) If players get used to only making rolls when they see the magic box pop up, then they'll be less likely to pay attention to the game - listen to what I'm saying as the GM, describing, requesting feedback/rolls from the players. Sure, players sometimes go AFK - but I'd expect them to flag that in FG (right-click on their PC portrait in FG) and let me know if they're going to be away for more than a minute.
But, like I say, this might be something that a lot of people like using in their games. If, for you st4lk3r87, it solves "[your] players having a lot of difficulties when [you] ask for a Check/Save/Initiative/Skill roll", then that's great that you've coded a cool solution to your issue.
Great work on the coding though. :) One question - how do you handle prompting players to roll when they are controlling multiple PCs?