Your story about coming out mimics mine very closely. Met what appeared to be my soulmate, wiped out my dysphoria, after awhile it comes back and I end up in a yo-yo relationship where I'm fighting between keeping her and dealing with the dysphoria. Eventually I came clean and it was the best decision of my life.
It's only been about 3 months since I told her, but she's been the best support I could have asked for. We had some initial communication issues, so it's important to not get angry because she doesn't say something the way you think she should be saying it. Taking her with me to counseling really helped a lot to get past the communication issues.
In just this short time, my confidence has shot up through the roof. Things about myself that I thought were too masculine are things she doesn't think are that big of a deal. That was one issue that caused some arguments because I thought she was trying to block my transition. It turns out she was right. I was the only one obsessing over those features. Nobody else noticed. She's helped to identify some mannerisms that are masculine that I didn't notice. She's helped me to pinpoint where my voice should be and to cultivate it. It's basically the same pitch as my natural voice, just spoken differently, something I never would have found without her. She's taught me how to do makeup and has taken me shopping for clothes and jewelry. I used to grab stuff off the rack and hope it's the right size so nobody would notice. She's gotten me to a point where I'm willing to try stuff on right there. She's also helped to remove the little bit of shame I had left by not being critical of me when I present as myself at home. It used to feel like I was doing something wrong putting on those clothes. Now they're just clothes.
So yes, I believe that it can work out, but you both have to be patient with each other. And don't sugar coat what you're feeling. This is as hard for her as it is for you, even if she repeatedly tells you it's not. I found it took a therapist to get her to open up about some things. When people find out about this, they hit the Internet for research, and they always find the suicide rate while they're reading about it. That leads them to hold some things back to avoid causing you depression. They mean well, but bottling things up just makes it worse in the long run.
You won't know if you need to transition until you try it out a little. I don't mean tell the world and start living life as a woman tomorrow. I mean try some isolated outings as your true self and see how it feels. For me, it was like suddenly opening my eyes. It felt amazing. Over time, the more I had to revert back to male mode, the more depressed I became. Was it a do or die moment? Not really, but it was bad enough to make me think I can't continue without doing the transition, so it probably would have gotten to that point eventually.
If she's comfortable with going out with you, I would highly recommend taking her. She'll be a natural confidence booster and people will be less likely be jerks with her at your side. Aside from dresses, the only people that seem to notice the difference between mens and womens clothing, are women. I'm not saying it doesn't happen, but I've been living about 90% as a woman for around 3 weeks now and have yet to encounter any snive remarks, strange glances, or anything else. The worst I've encountered is people gendering me female when I think I'm presenting male, making me not know how to behave. I live in the country where we have more churches than bars, which should be tougher for me than living near a city, but it's not.
I would also look up "Kristin's Trans Life" on youtube (it's a person, not a video title). I don't know who she is, but she compiled a list of questions, from other locations, that sound like a therapist would ask them. It really helped me decide whether I should transition or not.
