Yes it does take time. Maybe it is always a process, but one worth doing. If anything nothing bad will come out of it. The attachment thing is more like what Buddhism speaks about and it makes a lot of sense.
I have tried putting these things into practice and it took me quite a few times to really sink in, I really started noticing changes. But when I would stop and drift back to being the way I was before so did everything else. I just kept working at it, and it starts to become so much easier. But I still have to keep working at it all the time, but it keeps getting better. And then something will happen and it can set you back a little. So then you just have to regain that awareness again of what your mind is up to and where it is at.
If I start to feel down, or anxious or stressed, it is usually because my mind is off wherever it wants to go, thinking about things it doesn't need to be, things that might not even happen, or things that already passed. But when I being my awareness back to the present, without attaching to the emotions, it all the crazy making melts away with it.
Something that we always will have to work at, but it does get easier. And peaceful, without all that judging going on within mucking up our perspective on almost anything. I think some real healing can start to happen then because we become more open.
If you ever want helpful links or anything I can give you some. There are some pretty good videos on you tube too. But if you want to work on this just remember that it is all a practice, so if it seems difficult or anything just keep going, it will get better. I don't think there is ever really an "I have arrived" moment where we do it perfectly or without effort just as with meditation. It's all just a practice.
Dan I do care about you, I don't always know what to say but I know I hope that you can find that magical peaceful place, you and me and all of us. Those dang monks always look so peaceful and jolly even, has to make one curious about how they got there.

If they can get there, then we can get there too. I really think you can!
Kinda just thinking, maybe that is how we can be who we really are, and really be ok, and ok with that too. I know you talked a lot about having to fake it. And I am sure we have all done it at some point either a little or a lot at different times. Gandhi talked about when what we do, say and think all line up.. then we know true happiness, it comes from that harmony. My T told me the same thing, in different words, she called it being congruent, having your actions, words, feelings, and thoughts all parallel... being authentic which leads to contentment and peace. Genetic brought up the same idea the other day, with different wording... integrity. So maybe this can offer you a way to be you, and ok ... Like for real ok ( not pretend ok ) at the same time.