Ok, I know this sounds like an absurd suggestion at first, but hear me out. I am not suggesting that the dice roller is "broken" as it is, or that the random function needs work. The current dice roller is pretty good, and the random function is rock solid. But I think we can probably agree the dice roller has some issues. I have seen suggestions once or twice for changing something in the dice roller to work in a way that the user thought was more intuitive, and the response was basically "Sorry, that would break this, that and/or the other thing because of how it is written". Usually the things that would be broken were the macros that are already written for the way the system works now, so it certainly made sense to keep the dice roller the way it was. However, as more features have been added, some of them seem to have been limited by the need to maintain compatibility with the way other things were already handled. One example would be that we cannot combine math only rolls and regular rolls when using the drop/keep function. Another is the inability of the system to handle anything other than a basic number as the target when checking for success. Or the fact that  to add information to a roll dont work inside an inline roll. I am sure there is a reason we can list multiple specific numbers for a die to re-roll on, but we can only tell it to explode on > or <, but I can only guess what the reason is(no system anyone knows of calls for weird exploding like that?). One of the new suggestions you added, was to implement support for new dice mechanics(specifically re-roll once, I suggested re-roll a selectable number of times). But I have to ask, does it really makes sense to add more functions to the existing dice roller? It seems like you have already added a 2000sq.ft second level to a house where the first level is only 1000sq.ft and are looking to expand it even more. What I propose is not getting rid of the old dice roller, but creating a "Dice Roller 2.0" and having it be a selectable option in the campaign settings. Maybe it would be the default for new campaigns after it launches, maybe it wouldn't. Either way I think you should take a good look at all the mechanics you want the dice roller to support, and decide what is the best way to set up the interaction between each mechanic, and how the order of operations(or any other aspect of the dice roller) might need to change to make everything work together seamlessly. Then you might want to give some thought to how it could be designed to allow you to add new features without breaking anything it already does, but still let the new features work seamlessly with the old(I know, that's the hardest part).