Don't panic. Like anything she will take time to learn how to do it. 5 attempts, at least 2 successful, isn't too bad if my experience is anything to go by.
With our dd I ended up doing alternate feeds with bottle then boob. If the bottle feed didn't work, then we did boob. I did that for a couple of days and she did start to click. Maybe if you try it that way, would it take the pressure off?
My DH also couldn't get it to work in those early days and wasn't around to do alternate feeds throughout the day. At that stage I felt the barrier was her not knowing how to feed, not being confused about where the milk was coming from (she was 6 weeks).
I expressed fresh milk, just small amounts 1-2ozs, before each feed to give her. It was still warm when I gave it to her. I did small amounts so my boobs still had some milk left if she wouldn't take it.
I do share your feelings of worry about getting out in the evening and needing your own space. It was important to me too. She happily took a bottle up to 12 weeks old when she decided she didn't want it anymore! We had to give up again, but she did take the bottle again a few weeks later and we haven't looked back since.
It was very stressful, the whole bottle thing, until I decided to just try little and often and not to push it. Does that help? I guess the only disadvantage is the amount of time I spent expressing and sterilising in the beginning!
Good luck 