You have to do everything from the command line by ssh, unless you install a GUI which is not something particularly simple. Unfortunately I don't currently have the time to set it up (maybe in a month or so I will) for you but the process is simple enough. Go for an Ubuntu server. Once you have ssh'd into the server (on windows, get an app called winscp and do a search on how you can ssh with that app), make sure you're the root user ("root su", then type the root password provided by the company.
To install ruby: "apt-get install ruby". For mysql, there are plenty of guides online on how to get a mysql running on command-line on ubuntu so search for one of those and follow that. Make sure you create a user and table on the mysql that matches the configuration files in PE:O.
To run the server, navigate to the folder by command line and run "ruby main.rb".
Again, if you can wait a month, I might be able to do it for you then.
And don't worry about your 'cluelessness' lol. Everyone has to start somewhere, I definitely did. I'm more than willing to help, it's just the amount of time I can afford to dedicate is small.
Sorry for being off the radar lately, I've been very busy with other commitments. With regards to the VPS, pretty much anything will do. Windows or Linux will work, you just need to install ruby and a MySQL server and you should be good to go, the instructions in the PE: O folder are pretty easy to follow so I don't think you'll have any problems with that. If you do, just give me a shout on here or reddit and I'll see if I can help.
Also, how exactly did you make that gif playable during the intro scene? Whenever I try putting gif, it moves, but there's a white background even though everything's transparent(Gimp changes it into index mode instead of rgb). Tried to also save it as png, but that stops it from moving period.
It's all up and running (As far as I can tell from single player...) I can upload Pokemon perfectly. Can't really check looking for one and trading yet though. If you want to you should download and install the latest version of the script then I'll give you the link to use for the URL.
I'm not sure how that would effect it. You're game should work fine, but if anyone puts up a delta pokemon and someone from my game trades for it it would be an issue. You could add the deltas and special Pokemon to the BLACKLIST array to fix that though. Once he get's back to me and it's set up I'll send you the link to put in the script and we can test it out.
Since I still have no mysql or online knowledge I wasn't going to, but hansiec is being an amazing person and setting me up a server so yes! Are you thinking of doing a shared server between our games?