I'd like to weigh in on this discussion, even though I don't post here much. I lurk a lot, though.
In my neck of the woods, folks are pretty open to trying new things. It's not the complexity of the game that concerns most of the people I talk to. What it comes down to is getting them to suspend their DnD games long enough to try. No one is interested because of the Current Big Thing.
As for myself, I love RM. I've read all of the core rulebooks for each edition, as well as HARP, Middle Earth, Spacemaster, and even the cyberpunk book. And all of them have something good to take away. But I keep coming back to RMSS. Flaws and all, it still does what I most want.
It's the flaws, though, that have me interested in this discussion. I'm reasonably quick at character generation, for myself. With all of the bells and whistles, including Talent Law. But things slow down horribly when I have to teach someone else. Because there are so many steps, and each step has so many choices. Add in Talents and Flaws, and it takes even longer. Most people are okay with it, once they get to understand it, once they become familiar with it, but it's pretty overwhelming for a newbie. I think things need to be scaled back, for beginners.
Fewer categories would be a start. I agree that some of the categories seem pretty strange (like two artistic categories). A lot of the skills are so similar in scope and effect that they really don't need to be under separate categories. And honestly, Everyman, Occupational, and Restricted skills come up so rarely as to be pointless in the games I've played in. Better, I think to find some other way to benefit those skills on the few occasions that they do come up.
What I don't think needs to happen to simplify things for beginners is what happened in RMFRP. Taking some of the skill categories out, and then having to spend a large chunk of space in future books to add them back in seems pointless, and only intended to force people to buy the next book.
I like how stats are assigned in RMC (both temp and potential), but I dislike the way skills are purchased. As a player, I love to take advantage of the talents and flaws, but as a DM, all I see them adding is extra paperwork and munchkinism.
If I see a revised RM on the shelves, I'll buy it if it is complete out of the box, no hiding chunks in other books, like RMFRP. (And I don't mean I'm against new professions, etc. being in future books, just that I don't want to open the next book and find Skill X, which was left out for space reasons.) Instead of a combat chart for every single possible weapon, perhaps just one per category, with slight modifications applied to the results to vary the weapons themselves. Four or five core races, a few representative professions, and all the spell lists you need for those professions. Maybe as a boxed set, or slipcase set.
Finally, as regards software, I don't think it's a necessary project. If the number of steps and the amount of information needed can be reduced without going too far in the direction of 'simple', keeping paper forms, to me, is preferable. That does not mean, however, that I don't look around to see if there is something available (I google every RPG I play in to see what options are out there). I just don't think it needs to subtract resources from the revision itself.
I think I'm done rambling. I may think of more later. Just remember that RM around here isn't as difficult a sell as it might be elsewhere, which means that not everyone turns it down for it's complexity. Most often, RM just falls under "never heard of it." Maybe that's your biggest hurdle.