This issue actually occurs when you travel to Tatooine by other means besides using your ship's starmap (like using Priority Transport Outlaw's Den or also right now the stronghold's exit to Tatooine). And yes, before you have traveled there "the proper way" the game does indeed place a quest marker at the Anchorhead Spaceport, which for an Imperial character is obviously unreachable. However, once you travel to Tatooine via ship, the next stage of the quest is enabled and you can proceed to the shop (which is actually right next to the empire's spaceport). For further references, many swtor quests have this prerequisite to advance. You must travel to the planet in question via your own ship OR you must leave the planet in question via your own hangar at the spaceport or orbital station. If you don't, then the next stage of the quest will remain disabled.

I love this game and I love Star Wars but I cannot stop feeling there is something inherently wrong with the morality system presented by the lore, and this quest just proves it. It just goes against common sense. Supposedly the emotions always get you to the dark side even good ones like love, at least if you are a force user, right?. If you are strong in the force through emotions, you are strong in the dark side. But that's just a ludicrous simplification because according to the story it will make you necessarily evil. And the game allows you to be a "good" sith strong in the light side, but one that keeps doing emotionally things everywhere. Annnnnd the game let's you go around force persuading as a Jedi with no bad consequences at all. I mean that's just creepy you are twisting peoples minds and they know nothing about it. But if you are a sith and shock someone or force choke another, immediatly you get "dark side points!" because physical violence is really bad but telepathic meddling not so much apparently. And then again is interesting how through some empire quest chains you are explained that the jedi fear emotions and the sith just fear everything... so actually the dual nature of the light/dark dichotomy is just a great illusion ruled by fear and there is some hidden "middle path" somewhere, which is better. In the end when you break the suspension of disbelief with contradictory quest like these, you realize that the canon has huge huge plotholes, like everywhere! that yes, probably will be fixed sometime (retcon much?), but it doesn't mean they weren't there for starters.