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1 - Exit
Exit to Dreshdae (#12). Your goal the first time here is to speak with the guard at area #4 so that you can gain knowledge of the Sith Academy and how to enter.
2 - Academy Wannabes
You'll find three dimwits here providing Mekel at #3 with some entertainment. If you talk to them, you'll find out that Mekel has them standing out here until he says they pass the test. Once you speak with Mekel, return and talk both the left and right student into leaving their post for 2x (LS Points). The center student doesn't comprehend what you're trying to do and will stay.
3 - Mekel
Here's an ambitious student who turns out later to be one of your competitors. First talk to the students in a line at #2 to learn who set them up, and then return to Mekel and question him about it. He'll leave and you can return to the students to persuade them that Mekel was being cruel in return for Light Side points. According to a reader, you can Force Persuade the remaining wannabe to attack the guard as well.
4 - Sith Guard & Belaya of the Jedi Enclave
This guard is the man you'll want to talk to in order to gain entrance into the Sith Academy. He'll mention Yuthura Ban and that she hangs out in the cantina in Dreshdae (#11). You can then go and see her about entering the Academy.
Another encounter is possible here. If you killed Juhani back at the grove on Dantooine, Belaya from the Jedi Enclave (in the hub area near the exit of the enclave) will be at this sith entrance in Dark Jedi robes, and you'll then face off against her.
5 - Exit
Exit to Sith Academy (#9). Your first time in the Academy you won't be entering through this door. You'll instead "teleport" there with Yuthura, to Sith Academy (#1). After that, you can freely exit and return through this door.
After retrieving the Star Map:
The guard outside the door here will attack, but should pose absolutely no challenge.