Need other expertise RE: Windows and Joomla

I really hate to talk about Windows, but this is a different problem and there is a wealth of experience in this group.
I am under 2 kinds of NDA here.

Question 1: it appears that Joomla is not a real problem for Hype content based upon the posts here, but I would still appreciate opinions. Joomla has been used in this particular project before but I may not be able to get the original files to look at. If you have experience please tell me the strong points and weak points. I would like to convince them to not go that route. Do you know if there are any security weaknesses?

Question 2: Does anyone here have experience with Windows based web apps? The specification for the building workplace may not even allow a Mac in the building, I am not yet clear on that, it caused raised eyebrows. I know thats ignorant, but specs are specs and these people you do not argue with. Not that I won’t try for say, 5 minutes but you have to know where to get off the topic.

Is there an app out there something like Freeway, etc. Freeway for Windows seems to be gone. I don’t like the idea of Adobe or any cloud app, and it seems ludicrous that a cloud app would satisfy security concerns, but it may be the devil they know, so the devil may be transformed into a good guy in their minds.

I have to come up with an answer by 4/17.

I got my own question answered by Machighway, who is my webhost. They are going to provide me with all of the ISO (International Standards Organization) standards that relate to the requirements and I will just start training on Joomla.