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Hi there
Based on what you posted I see other questions. I'll copy what you posted and intersperse answers (and questions) inline.
I'm researching the next step (technology-wise) for our help files. Currently, I am using RH8 and generate our help using HTML help, thus creating a .chm file.
Fair enough. But keep in mind that the output depends on other unknown factors. 
The application for which I create help is Windows-based.
Windows-based. While I'm certain you meant that it only runs on the Windows platform, it could still be a Windows application that runs from a server. So the big question here is to ask where the application exists when the user runs it. Local PC or from a Network drive? If local PC, CHM is your answer. But if you want the help on the network, WebHelp or FlashHelp is the answer. More on this later.
So far, all of my research indicates that .chm files continue to be the standard for Windows-based applications.
Assuming you mean locally installed applications, that's mostly right. Again, more later.
Also, we use context-senstive help (click F1 in the field and the help for that definition displays), and we do not want to get rid of that functionality.
You don't have to. WebHelp, FlashHelp and AIRHelp all have the same functionality.
That is another reason we are stuck with .chm files--it's the only format I'm aware of that allows context-sensitive help.
Nope. As I said earlier, CSH exists in many shapes and sizes.
I suppose my question is if anyone is aware of a "newer" and more "modern" output that still allows me to use context-sensitive help.
Yep. WebHelp and FlashHelp are newer and more "Modern" looking. So is AIR Help. What it boils down to is how "Modern" you want it to look, as well as other factors I'll describe later.
Also, our developers may be using Silverlight in the future--not sure if that will have any effect on my research or not...
I'm not sure about Silverlight either. But it seems to me that Silverlight is falling by the wayside. I base that judgement on viewing some popular web sites that once had Silverlight apps running, but have since moved back to Flash. I'm guessing there is a reason they made that move.
It would seem to me that AIR Help may be what you are looking for here. But only you can decide that once you know its strengths and weaknesses.
Strengths:
Looks newer.
Able to easily update help later.
Able to use user added commenting if using the locally installed AIR Help.
Weaknesses:
Must be installed like an application
In addition to each user having to install AIR Help, they must also download and install the AIR viewer application prior to installing the AIR Help package.
Must have a digitally signed certificate - Allows one to be created, but it's not the same as purchasing one. Users may be hinky over that.
Not easily customized. You are bound by the look and feel Adobe decides to offer. They do offer some customization, such as adding a Company Logo, but you cannot change the colors or the layout.
I don't believe user added commenting is possible for Web Based AIR Help.
User commenting isn't easy to discover for locally installed AIR Help.
There is more on the AIR Help format over on fellow Adobe Community Professional Peter Grainge's site.
Click here to visit Peter's site
Cheers... Rick 
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