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Pause just for a brief second and consider the name of "VSS". It means "Visual Source Safe". This means it is designed to act as a Source control system.
Your projects are made up of Source files that you use to produce Output files from. The Output file(s) could be .CHM format or WebHelp format or FlashHelp format.
While I have certainly heard of folks placing their Output files in a Source Control system, I'm going to crawl way out here on this shaky little limb and say that it's certainly not the norm, nor is it desirable in most cases.
The bottom line here is that you should probably consider only storing your project Source files in VSS. Place the .CHM somewhere such as your network, so that folks can copy it to their local PC for viewing. (.CHM files have issues nowadays with being viewed from a network).
I do place my .chm file in VSS, but that because the developers need them in there to do a build for our software.
What I've done is create Application 1 , Applicarion 2 and Application 3 sub-directories. I then manually cut and paste the chm files over there from the output SSL directory of Robohelp. This makes them available to the developers - I do this every few days to keep my version for them reasonably up to date. .
Reason I do it that way is that if you regenerate the project from Robohelp and you've checked the .chm files from the ouput SSL folder into Source Safe, it's easy to forget to check out the chm files from Source Safe before you do regenerate.
I merge several sub projects into a master, and this result in a file with a .chw extension being added into the output. If this isn't checked out before you regenerate, indexes, see also's, etc, tend not to get updated.
RoboHelp seems able to identify that VSS is on the system - when I checked my Robohelp source files into version control, it selected VSS automatically.
I would definately consider putting your source files into VSS - i give me reassurance that if I do something terrible to what I'm working on, I can get an earlier and non-corrupted version of the source files from VSS.