On some level, not remotely, and on another level absolutely. If you're on major runs between planets, then it's fairly safe because if something happens and your ship just breaks down, then likely someone else is going to come along to hear your distress call. On the other hand, if you're not on a major run, yeah - if something goes wrong you might just never be heard from again. It's a good idea to know your ship pretty well and be able to do minor repairs, carry supplies, and so forth. There's also pretty good communication between places - but it can be dangerous I suppose.
He used to be. There was a rebellion and the Empire was replaced with the New Republic so I've been on my own for a while now.
One of the first rules I give myself is to know my surroundings, so I went out several times just to get the feel of the city. We could start with caf coffee if you'd like?