What is the functional difference between player program and web-based?
In the short-term, Realm Works Player Edition will have more features available than the web app. Realm Works Player Edition is based on the existing Realm Works GM Edition, so we get to reuse a lot of what's already there. The web app is being written from scratch. Generally speaking, our plan is to roll out features to the web app over time. So the initial version will be very limited, but will frequently get new features added as soon as they come online. The goal is to make it available as soon as it's useful, rather than holding it back until it can do "all the things."
Another important thing to keep in mind is that the Player Edition desktop client will be usable offline, just like the GM edition. You'll be able to sync the realms you're in, then use them "on the go" without needing a constant internet connection. The web application will not be able to do this. For many people, this difference alone will make Player Edition worth purchasing. A reliable internet connection can be hard to find at a convention (or in a friend's basement), and mobile data plans can be expensive if you make heavy use of them.
Can both be used for player journals and session feedback?
Eventually yes, our plan is to allow players to view and author their own journals, both in Player Edition and on the web. They will probably not both become available at the same time, however. You'll almost certainly be able to write player journals in Player Edition before you'll be able to in the web app.
I'm not exactly sure what you mean by "session feedback". I assume you mean some kind of private message to the GM?
Do they look/feel different?
Player Edition is based on the same interface as GM edition, so they will look and feel very similar.
As for Player Edition vs the web app, they will certainly look different. The desktop clients (GM and Player Edition) are visually very Windows desktop-focused. The web app will be running in many different browsers on many different devices with different operating systems. We won't be going out of our way to try to make the app running on these varying devices "look like Windows". Expect something closer to a traditional web application (Facebook, Twitter, YouTube, Gmail, etc).
Do they match the GM program in layout?
Will they remember views?
Again, Player Edition is based on the same interface as GM edition, so the layout will be similar but with appropriate functionality disabled or hidden from players (no revealing the evil mastermind for you!

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The web application will have a number of differences to provide the best browser-based experience. This means you'll be able to use your browser's tabs, bookmarks, favorites, history, back button, etc. This will necessitate some changes in behavior and layout between the desktop apps and the web app, simply because whatever browser you use will be "in charge" of those things, rather than Realm Works.
We're also aware that Realm Works is pretty complex and can be daunting to newcomers. The web app will initially be focused on players, so we may also be experimenting with some possibilities to make it a friendlier experience overall. If we find some changes particularly helpful, they might find their way back into the desktop apps too.
What is the value add of a standalone product?
I'm not sure which product you're referring to, so I'll assume you mean Player Edition and you can tell me if you meant something else. I think I answered this above, regarding offline use vs the web app.
Can players print materials?
Can players access their characters in HL via RW?
I don't have a solid answer for this. We don't really even have these features in GM Edition yet, so it's unknown how it will unfold.
How granular will the player view be - by player, by realm, by character?
I don't understand the question. Currently, Player View is the feature that allows GMs to display information to the players on their PC or a second monitor. Is this the feature you're referring to, or something else?
Since GM is already paying for cloud space, this feels like double-dipping. Is it?
Unfortunately I'm probably not the best person to answer this question. Hopefully someone else *cough* Liz *cough* will help me out.
