Thought I would post a update.
TL:DR In the process of going for it. Why let fear of failure let me be happy.
Pros:
1. Lack of area's to practice: I'm getting better with finding places to practice. I'm also learning that time of day plays a role. So adjust my schedule to when (insert place here) is jumping. Also I'm trying to find events to go to. I might not meet anyone but I can arm myself with a skill. So far it's working out ok.
2. Age Gaps: Unless they look like they are in HS then screw it. I'm under no obligation to marry/screw the first person I talk to.
3. Cold Approaches: Marked improvement. I hate using canned stuff. So I try to be natural about it. So far it's working ok and confidence is getting better. What I started out doing was looking for an IOI and then started the approach. I can now go in sans IOI and try to get a convo going.
4. Inner game: I've been hitting this really hard. Looking back on my life (and no I won't post details) I realize that I'm a hardcore badass. It's just that I'm too shy/modest.
Stuff that needs work:
1. Bars and clubs: Out right fail! Too many reasons to list. But I don't want to eliminate my options as I want to be good in all areas. So my intent is to hit up a few clubs tonight.
2. Online: Bottom line pics just suck. I went out with a friend to get good online dating pics. From the results I look too tense and lack eye contact. Again this is being worked on. I'm taking selfies where I look more natural. The pics arn't being posted anywhere (again practice). On another sidenote dear lord I need new cloths. Since dieting and working out my nice cloths fit too big (worse still I'm between sizes). Guess I need to stop getting fit and go on the McDonalds diet

(or buy new cloths and use the opportunity to practice).
3. Groups: This is what I want to spend more time focusing on. And I feel is the biggest issue. Any help on this would be appreciated.
4. Time: Ugh to have responsibilities. I work four ten hour days and have three days off (that down time is spent on working on the above). Despite this is why I want to incorporate online dating.
That being said I'm aware this is a long and challenging process. Much like anything there are times I'm going to suck (and there have been times). And times I've won minor victories. I must remember not everyone moves at the same rate. But overall it's been fun. I just have to keep getting out there.