Most of the time, the CPD file (cache) file is in the way. In the RoboHelp options, please select the option to always clear cache before opening a project. That will require RH to always rebuild the cache and have it pick up new files.
I suspect that this may also solver your first issue. The cache simply isn't up to date with the latest changes.
Thanks for your feedback. I checked the box to clear cache before opening the project and then re-opened the project. The following files still did not update on the Outputs(SSL) pod in RH for the project:
(There are many more ssl files that did not re-load into my local version of RH via the Outputs(SSL) pod but I only listed a few above.)
It looks like somehow my SSL files were overwritten in TFS so now we are trying to bring them back from history.
I'll apply the "clear cache" checkbox to my coworkers to see if it clears up the issue for them with broken links.
Also make sure the .cpd file is not in TFS as this causes all sorts of problems. (And remove the .ldb and .pss if they happen to be included, too).