As with the above assumption on how our cloud platform works, this is also incorrect. We dont actually support any environment. We support the product, and state the following
The added line related to windows server is in absolutely no way at all related to how its set up. Its related to the fact we have seen on many occasions issues when people are using IIS. Usually surrounding things like permissions etc, but often related to the underlying server setup. Not necessarily just IIS.
I have to admit to being a little confused as to why you believe this to be the case? We don't "spin up" a new box when someone creates a new cloud instance. Its essentially just an account. While it will have it owns files (things that people have uploaded) and its own data, it doesn't necessarily mean it will have its own instance of the software. You are thinking of this in terms of an installation that is done on self hosted, and cloud just doesn't work in that manner in any way.
We are not likely to get into the decisions made on a daily basis for each items we decide on. Its simply not feesable. We have too many things we make decisions on daily. However I can put this into some context for you by asking you a simple question. If in your job, whatever that happens to be, you could do something that would add nothing at all in terms of value as a company. Would you do it? The reality is, the 'self-hosted' product is a shrinking market. We have made changes to the licensing to ensure that its viable for the immediate future for our customers. But we need to be selective over what we spend development time on, and things such as these are not really of huge value.
Note again, it's not a decision that I would personally make. However I'm giving you the reasoning why its probably unlikely.