I think a Wiki could work, but I would start it out as a private wiki, on the wolfair.com domain and only those who purchased the software can edit the wiki. A small team of trusted volunteers could be made moderators to ensure consistent quality. That would go a long way towards creating a *comprehensive* set of documentation without overly taxing and distracting the development team. Unfortunately, it won't help new users that much.
As a new, but rather intense OCR user, I've spent, easily 16 out of the 48 hours since purchasing the software moving content into it, reading/viewing available documentation, and reading and posting on these forums. Here are my observations:
The tool really is awesome. The advertising copy does a good job relaying that, but when you actually buy, download, and start using the software, I felt like I jumped into the deep end of the pool. A big part of the reason for this, I think, is that the software developer's paradigm is lost in the thicket of details. Also, there seems to be a lack of examples and walk-throughs.
I don't mean to ding the existing documentation—it is good. As I became familiar with the program, and went back to the material, I found them very very helpful. But there wan't any thing that really eased me into the program.
As an example of great intro/new-user documentation for a highly flexible, feature rich, application, I would point to Wrike's documentation (
https://www.wrike.com/help/). In particular, their on-boarding documentation is excellent. They explain their paradigm and product vision in clear terms and then introduce the interface and main features in that context. Also, their examples and walk-throughs are especially helpful. I also like their online design that integrates bit-sized video into the text, but also provides well designed PDFs for printouts.
Given limited budget and time to even oversee end-user volunteer work, I would prioritize the following:
1. Use Case Studies. Have your users show other users how they used the tools in their campaigns. This could (should) be a combination of PDF and video. Each use case should include an explanation of the kind of game and style/philosophy of play, and explanation of how they structured their data, how the tool has helped there games, what features have been particularly useful, and tips and tricks they can share. SEEING *EXPERIENCED* game master who have a deep knowledge of the tool walk users through the tool is very helpful. The existing videos don't do such a good job with this. Like others have mentioned in the forums, pausing the Gencon videos (I watched them all) was helpful, but that's A LOT of video to go through for a few screens worth of examples.
You would want to invest some time into ensuring consistent quality and branding. But you should be able generate a lot great end-user content with a contest. Ask your users to share information about how they built their worlds/adventures in RW, with specific elements that must be covered and to keep the videos to say 10-15 minutes. Have the forum community vote on the best, and the winner(s) get free player licenses, or a years subscription to your cloud service, etc.
2. The Wiki. This is a bit tougher, since you don't want half-baked content reflecting poorly on your brand. Perhaps try it out as a non-public wiki until sufficient quality content is available. Again, give awards to your best contributors. I think this is an easier approach than managing assignments to volunteer content creators.
As a new user, I've been impressed with the responsive and detailed responses I've received to my forum posts by your users. You already have users making videos on how to use your product. I think you can leverage your users to do a lot of the heavy lifting on this.
