I feel that, as someone having administrator access to the skylines infrastructure, I have some insight.
I also own a full backup of all IGC files by the way, because I ran into problems while dealing with OLC.
The same also applies to our local RASP files. Anyone interested in parts of the data, feel free to contact me.

Try serving a sandwich to 47 friends at a party, and to do it for 2396 people. Organization changes, a lot.
That is true. In terms of this party, the changes start when you cannot perform all tasks by yourself.
Or, in the case of computers, when you need multiple computers. Especially when you need more computers than you have components (database server,
webserver, etc) in your architecture.

The skylines server is rather idle on any given moment, so the point where one would need multiple servers is not near.

I heard that Skylines is rising 10k euro too.
Since the birth of SkyLines I have not witnessed or heard about any money being donated or otherwise obtained from third parties.
Given the fact that the source code of the whole system and its contents are freely available, I also find it hard to imagine how it would "rise" money.