I'm interested in the first scenario to avoid with nested offline availability. I've inherited a setup like this where everybody has a home folder mapped to a network drive in AD. The documents, desktop, pictures, etc. folders are located in that directory and folder redirection is set up, making them available offline. The mapped drive is also made available offline.
What problems have you observed from this configuration? I have seen a problem at times where the files show offline and synchronizations seems to break. I'm not sure if it's gradually or what but a user will call and they have a bunch of gray Xs over their files and a lot of things are missing. If they're mapped via DFS, this path won't be accessible but the actual file path using the server name will be online and available or vice versa. Is this the type of problem caused by the configuration mentioned in the article?