I'm a 31 your old guy, been single pretty much my whole life. Here's a quick rundown of my qualities:

The good (NOTE: please don't take these as boasting, I'm trying my best to assess myself objectively based both on my own and others' impressions): I dress well, reasonably athletic, successful in my career as a freelancer (but switching right now due to burnout) and do well financially, intelligent and sophisticated, good sense of humour, make a confident impression according to others, have a deep voice I frequently get compimented on.

The bad: I have serious self esteem issues, I'm prone to anxiety and depression, I get easily frustrated and sink into feelings of hopelessness and frustration, I'm very confrontative (not always a bad thing, but it doesn't help in forming lasting social ties), I pedestalise beautiful women both consciously and unconsciously, and I feel lost and helpless in large social situations like parties or crowded bars, festivals, etc. I'm also very inhibited (if you haven't guessed already).

The not-necessarily-good-or-bad-but-I'd-rather-not-be-like-that: I'm 5'9 (feels like everyone's a fucking giant nowadays), I have somewhat of a baby-face (people regularly take me for being 6-7 years younger than I am), can't grow a beard to make it look more mature, have submissive sexual desires/fantasies (again, not objectively bad, but in my experience most women like men who act dominant not just in life but in bed too).

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I've had a quite successful investment lately, and I decided I'd use the profits to take a break from my routine lifestyle for a year or so, and work on the parts of my life that I've been neglecting. One of the most important of these is dating. I have many repressed insues and unresolved anxieties around meeting women, and I know I'll have to face these sooner or later if I don't want to grow old lonely and yearning for something I cannot have. So I want to work on this in the next period.

What I'm asking for is tips on how to start out, maybe resources on how could I do this effectively. I've read a bunch of PUA/dating books in the past 10 years, so I'm not really looking for actual game tips, but rather on how should I create a plan of action to work through my inhibitions and anxieties.

I'm prepared to put as much effort as needed into this, but I always needed a systematic action plan that I could trust in order to be able to do something with conviction, and I'm asking for your help in compiling this plan.