Good advice, but I was looking for more of a solution to the barriers I feel bar escalation. A mindset or truth that will help me know whens a good time to make a move. I thought I was past this honestly, but without actually being able to escalate to something frater than holding I feel stuck

There is no right time to make a move, you have to make that time.

Be playful at all times. For example, push her gently when she says something funny or just touch her shoulder, play with her hair when she gets intimate, hug her when she says something amazing, just do anything in order to break that touch barrier between you both. The more you touch her, the more secure she'll feel around you. When you reach that level, try to be physically closer to her while talking (sit closer to her) so that your body is touching hers. She'll directly start getting turned on. At that point, you have to take the risk of all in. You gaze from the eyes to the lips in a triangular motion, if she keeps looking for more than two seconds or so, go for the kiss.

That's personally how I do it, and it works.

In short, you should be willing to risk something to get everything.
If you don't risk it, you'll never know if you would've succeeded or not, and it'll haunt you all the time.

Hope this helped