I stopped going down this path after the third client in a row who was so disorganized that "oh, sorry, didn't tell you about that GPO/NAT/firewall...". Usually after I run smack into it and start asking along the lines of "it's as if such-and-such is blocking thingamajig". They completely understand that when they spring these surprises on me, the contract price goes up; it doesn't faze them in the least, it is part of the landscape for them.

At the same time, they refuse to consider appliances or SaaS-oriented solutions; everything has to be on-premises and built from the ground up with them performing the remote fingers (and honestly, performing the steps without really understanding them).

This seems to be a widespread requirement in US Federal Government contracting circles, so I'm surprised there isn't some kind of telepresence solution that lets you type a command and passes it through after the staff member presses the "y" or Enter key to accept, and prompts in a similar fashion for each mouse click/drag. Maybe even record each approved step.