Legal Issues: Some games are published under a license that allows sharing Mechanical content (ex. Pathfinder, D&D 3.x, etc., allow sharing of monster stat-blocks and rules elements); content like the setting (Forgotten Realms, Golarion, etc.) and adventure plots/stories are not included in that "open content". Other games (such as Traveller 5 or Star Wars d6) are not published under such a license - any sharing of their content is problematic. Even when there is a license, it usually has some requirements that must be met before the content can be shared.
If you're thinking of sites like d20pfsrd, that's an example of the open license in use. They can share mechanics, but not protected story content. Because of that, they need to sometimes re-name things that have protected names, which occasionally leads to frustration for people looking in HeroLab for the wrong name because they saw something on d20pfsrd that they want to use.
The Cloud: Unfortunately, LWD used the term "the cloud" for something most people would not think of as "the cloud". "The cloud" to many is synonymous with DropBox, OneDrive, GoogleDrive, or similar internet data/file storage services. That is not what LWD meant, and they are replacing the terminology wherever they find it in their literature in order to reduce that confusion.
HeroLab is file based - characters. monsters, and encounters are saved to *.por files that can be moved around, copied, etc., on DropBox, OneDrive, GoogleDrive, etc. Realm Works is NOT file-based. There is one file that is tied to the Windows User account... it is not movable to "cloud drives" and would not be accessible even if it could be.
Lots of people hope for live updating .. it is mentioned often in the Feature Requests forum. How soon, if ever, that might be is not known at this time. RW was designed to be for player use mostly between sessions. It has some features to do "live" showing (Player View on a second monitor seems to work), but it does not broadcast updates to clients as a VTT would. Using a VTT for immediate reveal in parallel with RW for between session access to information is a workable solution as well -- and there are requests for tighter integration with VTTs as well.