I’m a bit confused to how this works…there is a guy in my country who has advertised Cubase 9.5 for approx. 300USD online.
He says that you (purchaser) will only get his e-licenser usb stick and have to download Cubase from Steinbergs website (feels very shady).
What I don’t understand is that I’ve found sites selling a e-licenser usb stick for like 10% of that price!
So you only need a copy of Cubase from steinbergs site and a e-license stick? I’m surely missing something here…can’t possibly be that easy 
No it is not that easy: You need a license stick with a valid license on it, which a simple eLicenser does not have.
The e-licenser is hardware only . You can see it as an empty device with no license on it. So when you have this e-licenser you can buy a product like Cubase and store the license of this product on it. Both are required to run the product. So actually buying an e-licenser only will not give you Cubase. Comparable with buying a usb stick with nothing on it.
Ah I see! So you download Cubase for free and pay for the e-licenser?
Not quite.
You can download a trial of Cubase for free (but you need an eLicenser even for the trial with Cubase Pro and Artist).
Your trial license goes on the eLicenser. After 30 days the trial ends.
If you wish to purchase a Full Cubase license, this purchased license goes on the eLicenser you already bought.
You pay for both the physical eLicenser and the Cubase license that goes on it.