Hello Carl,
I am not able to answer your specific question because Windows development is not my area of expertise. I will try to describe an alternative approach.
First, let me ask, what kind of documents are you managing in "simpledms"? Is that modularized XML / DITA with single-sourcing and translation management or is it office documents?
We,
simonsoft.se, develop a CCMS specifically for XML / DITA Authoring / Release / Translation / Publish which uses Subversion as the underlying database. It provides a Web UI that is DMS/CMS-centric rather than code-centric and we additionally allow users to manage files with TortoiseSVN, primarily managing graphics for the XML documents including the aspect of translated graphics (can be massive amounts of screenshots for some customers).
We would also be interested in making TortoiseSVN as friendly as possible for non-technical users. I don't think we would go as far as a custom installation though. I think the Settings -> General -> Context Menu is an interesting place to tweak. Enabling a number of actions for the context menu can enable most users to never need the TortoiseSVN submenu (e.g. Show log, Get lock, Add, Import).
There is a sync feature for TortoiseSVN settings. I would be very interested in the ability to configure TortoiseSVN from a Tsvncmd URL but the sync action is not available. Could be a security consideration?
Perhaps we could add the ability to configure non-security settings from a Tsvncmd URL (perhaps triggering a settings sync getting the settings file from an https url).
Thanks,
Thomas Å.