I've noticed the RPGaDay thing once in a while for a bit, but it's only 
(questions and image from autocratik.blogspot.com)
I'm going to go back and do the week I missed before the end of August so that everyone can see my delightful insights (or maybe not-so-delightful insights, but hopefully I can be forgiven for optimism in marketing), but I want to start right now with the question of the day so I can be in alignment with everyone else going forward. Ironically, my power went out for several hours while I was working on this yesterday, so I'm actually posting this a day late. I'll try to catch up on the weekends.
Real Games, Realistic Requirements for Entry
One of the issues that I often find with getting players into roleplaying is that a lot of games aimed at "novices" or "non-roleplayers" and have a simple ruleset are also really simple as part of their storytelling conceit.
I'm not necessarily against these games, but I think that something like this can backfire, because they may have light rules, but they're more narratively complex and require players to invest heavily in a particular setting or genre before they can really flourish in the game.
Lady Blackbird is an example of this. It's a fantastic, wonderful game, but I always wince a little when I hear it suggested to novices.
Why?
Because it has a lot of opportunities for experienced players, but novices are stuck as pre-made characters in a setting that doesn't give a whole lot of creative latitude.
In my experience, players not getting to fulfill their own concepts is one of the number one reasons why people turn away from tabletop roleplaying. If you're not going to have the ability to make your own decisions and use your own characters, then there's really no distinction between a roleplaying game and a more traditional video game.
Sure, there's a social aspect to it, but you can find that in some video games, like MMORPGs and other group-based games. For someone not accustomed to storytelling and pushed into a pre-assigned role, the dynamics of such a game may even lead to a better experience.
KISS
One of the things that I think designers need to do a better job at is keeping things simple. I know I'm not, by any means, an expert on this subject, and I probably am a little bit hypocritical for harping on about it, but there are real issues with regards to the investment many games require players to begin with.
D&D, for instance, is relatively easy to make a character in, but also has a bunch of individualized rules for each character. I don't know of many DMs who can help players overmuch with their rules reference. They can maybe help one or two players with classes that they are familiar with, but being comfortable enough with any particular class and background to help players with every concern they may have is difficult.
There's also a lot of ambiguity in some things which build to quite a spectacle in some situations (most humorously the somewhat unclearly titled Cleric ability "Turn Undead") and just create headaches in others.
Foremost, however, the problem with D&D is that you can't necessarily ask players what they want to play and expect the system to acquiesce neatly. Punching things? Monk, maybe. But there are build issues there, and you don't necessarily build a good monk with some of the builds that focus on punching things. You could consider a fighter or barbarian, too, but there's no guarantee you'd be competitive with others even then. To fix this issue, you make the game more complex by adding in additional rulebooks or house-rules, or there's this nifty thing I found online...
Get my point?
This isn't unique to tabletop RPGs, but it is something that is exacerbated in them because players are theoretically building a character with an infinite canvas of opportunity.
In a video game, one can be forgiven for locking players into a particular path. Where it makes sense, you can forbid things in either medium; you wouldn't necessarily expect magic in a cyberpunk game (except when you do, coughShadowruncough). There is a limit to the technology you can find in the James Bond adventure. You may never be able to jump the Empire State Building in a single go.
But the problem is that many of our games are nominally designed to "let players tell their stories" but don't really do that at all when you get down to it.
I'm going to plug Open Legend (which I was a very, very, very minor contributor to) or my own game Hammercalled (free Quick-Start available on DriveThruRPG!) as an alternative to this.
While they rely a lot less on pre-defined systems, which often serve as guides to players, they allow players a lot more freedom in actually choosing what they want to do. I even think that they work better than "point-buy" systems because they have a lot less stuff to define; Open Legend eschews most skills entirely, and Hammercalled has them, but makes them entirely individually defined.
There are still some minimum complexities you hit when you're making a game that has an appealing amount of crunch for some audiences (I am a member of that audience that likes a little meat on the bones of my games), but you'd be surprised how much what is typically considered "simple" is really complex to an outsider.
A Better Face
Fortunately, roleplaying currently has a reputation that no longer involves malodorous basement dwellers (or at least not exclusively, as it once had).
However, there are still things that people could do to help grow the community, and some of it is individualized.
Let me start off by pointing out that I'm not trying to condemn anyone or anything when I say this, but it's hard as heck to get into the tabletop roleplaying market.
Too many of the major games are not available (legally, which is where you get an ironic twist, since pirates have long had access to almost anything they want digitally) in a convenient format, due to licensing concerns. There are a lot of people who would love to play a roleplaying game, but don't want a large hardcover book.
If I want to play D&D 5e, I can now, finally, do so using an online reference in the form of D&D Beyond, but it's always online and is not necessarily as accessible as one would hope, clearly being intended more for use as supplemental to books rather than a true alternative (at least in my opinion; I find the books easy to read and D&D Beyond to be frustrating). There are other things, like Fantasy Grounds, but this requires another major purchase on top of the other purchases, and locks players into always using an electronic device at the table.
However, many other major games, including licensed titles, are not available in traditional digital distribution platforms. The most notable of these include the Star Wars games, but there are enough that it's worth at least considering.
Let me start this next bit by saying that I love DriveThruRPG a lot, and they've always been nothing but great to me.
DriveThruRPG is not the Steam of roleplaying games.
I really hope that at some point they do some major overhauls; I think they've got a good setup right now, but there are so many more convenient digital distribution methods that don't match up. It's a bit of a pain for me to go to DriveThruRPG and download a title from it, and once I download it I have to manage my files myself. There is a desktop app, but it's Windows only (not a problem for me), just a library browser, and lags behind the website in usability. It also has weird issues with some files, leading to it showing a bunch of stuff downloaded that I have not downloaded and not letting me download them.
Ultimately, I think that one of the things that would be best for the industry would be if a large platform for games like Steam started distributing tabletop roleplaying games. There are issues with that model given differences between video games and RPGs, but right now I think a lot of people don't even know where they would get started if they wanted to get into tabletop roleplaying, and there's no good solution to that currently.