I train guys around the world with this exact problem all the time.
The main problem is that you are thinking about dating the wrong way.
You thinking about dating logically, like looking at yourself from a 'on paper" point of view, thinking about getting a girlfriend, not being able to hold onto a girl, kind of like dating is a process similar to getting a job, or getting a girlfriend has something to do with having an house, or the money you make, or your job or something.
Let me tell you, dating, and pickup, is not a logical process at all, its a primal, instinctual and emotional process that has little to do with those things. Those more logical things may help if you already get the emotional triggers stuff down, but really most of the guys I know who are totally amazing about women are actually pretty broke.
Your main issue reading your post is that you are not dominant enough. To be good with women you generally need the ability to approach, and touch women properly to have any chance. Often you need to be downright bossy and a fairly persistent to push through the layers of resistance women tend to have.
When I think about dating, and 'pickup', I think about it as a physical thing. Many guys when they visualize how to do it, or what dating or approaching women is like, they think they walk up and start talking, like dating is a conversational thing. Sure you need to do that too, but in my brain pickup is pretty much entirely a physical thing. Your success all comes down to how you touch her.
In fact, many successful guys get women who like them, but really if you miss windows of opportunity or you get attraction from girls but you fail to pull the trigger women will lose interest. The more socially popular the women the smaller the window of opportunity, and the quicker you need to respond.
When I started getting good at this, and am now at the stage where it is really easy for me, and I really get overwhelmed with the amount of girls who like me, it surprised me how fast this whole process occurs, and how less-formal it is. Guys seem to go way too slow generally, and think that its like a job interview or something, and they are just generally way too serious, and the thing they talk about like, pow.
Matt
Dating Tips for Men: EXPOSED