Yeah, good man you've done a lot of work here to set out a plan and goals for yourself. Most self-improvement books I've read start off by making you do this, so it's a good start.

The only thing I would say is you seem to be putting quite a lot of pressure on yourself. If you try to do all this at once you can burn out and end up frustrated. The books I've read usually ask you to prioritise which areas you want to tackle first, so you can put time and energy into them while keeping the other areas ticking over until you get around to them.

On your questions..

For recommended reading here's a few great books IMO that you can get as eBooks:

1) Cognitive Behavioural Therapy: your route out of perfectionism, self sabotage and everyday habits by Avy Joseph

2) How to Succeed with Women by Ron Louis and David Copeland

3) The Confidence Gap: from fear to freedom by Dr Russ Harris

My first approach ...it wasn't that long ago - drunk on a train - sat down opposite a cute girl - asked what book she was reading - it was some kind of murder tale (can't remember what) - I took that as a hook and started talking about murder books I had read, then got inside my head and clammed up. She got up and got off at the next stop (don't know whether it was her stop or not). I don't think she was too impressed!

Still, first one out of the way and all that