Upgrading Server directly from Mountain Lion to Yosemite?-

Hello all,
I have a Mac Mini running Mountain Lion (10.8.5) and Server (2.2), hosting a small private webserver (PHP + MySQL), VPN, some LaunchAgents cron jobs, and file sharing service. I'd like to upgrade it directly to Yosemite and the latest Server app (4.0).
However I'm not an expert in server stuff, and I'd like to be sure that the direct upgrade will correctly migrate all my current Server settings. I've fiddled with the settings over time (including files like httpd.conf or php.ini, or adding self-signed SSL certificates) and I don't think I could easily "recreate" them from scratch if something went wrong…
So here are some questions:
"Software update" is suggesting me to upgrade to Yosemite, which is fine, but does not suggest me to upgrade Server too. Is this normal? I know that Server is a paid upgrade, but I'm surprised there is no automated upgrade process in my case. Also, "About my Mac" shows my OS version as simply "10.8.5", without any "Server" mention, is this normal too?
If everything above is normal, I suppose that the safe and normal way is upgrading to Yosemite, and then buying normally Server 4.0 in the Mac App Store?
In case something goes wrong, is there a way to "export" all Server 2.2 settings in order to import them later in Server 4.0?
My Mac Mini is headless, managed through Screen Sharing on an iMac. Can the upgrade to Yosemite be done without an actual monitor? In other words, will the "Screen sharing" service on the Mac Mini still be enabled? If not, will the "target display mode" work, using the iMac screen and a Thunderbolt cable?
Any help is greatly appreciated. Thanks!

Technically, you can downgrade if you have the following:
Your computer must be elligible to run Mountain Lion. If your computer came with Mavericks or Yosemite out of the box, you can forget it.
You need an already existing Mountain Lion installer file. If you still have that somewhere, for example in your Applications folder, or anywhere else, it's usable- note that it needs to be originally downloaded with your own Apple ID and password. If you made a Mountain Lion USB installer or DVD back then that would work too. If your Time Machine back-ups go back to the days of Mountain Lion or Lion you could check your Applications folder from inside Time Machine and restore it to your computer.
To not have data loss you need a Time Machine back-up that goes back to when you were still running Mountain Lion. Please note that this will revert your data to exactly the date that you choose. If you installed Mavericks 2 months ago, you will loose 2 months worth of data.

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