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I think you are trying to do and understand too much. I do not believe it is generally productive to develop a theory on what "women" as a class do- or do-not like; the category is simply too large and too diverse. And even if some general trends can be discerned, they are not likely to be specific enough to be of more than marginal assistance in any given interaction with a random woman. Moreover, geographic and relational clustering effects (i.e., local, ideological, or subject-based sub-cultures or groups) can result in highly heterogenous pockets with unique and/or counterintuitive dynamics, separate and apart from the main trends.
Here is my advice to you:
make yourself as interesting and capable a person as you can - whatever that means to you. Acquire skills. Get in good shape. Learn to dress and present yourself well. Ponder the mysteries of life until you have something interesting to say. Read great writers and prose stylists until you can command language well enough to express your thoughts clearly, concisely, and interestingly. Learn about (or, better, go experience) some interesting shit - not like "I went on holiday to Cambodia and man are the Phnom Penh temple complexes cool!", but instead put yourself in new circumstances that will test or surprise you. Push yourself to- and through- your limits. Get some interesting life stories, and then learn to tell them well. You should be doing this anyway, and if you are doing a good job it will have the happy side-effect of drawing other people to you. People like interesting, competent, attractive people.
interact with women as individuals. Personally I've always found it much less daunting to talk to "Jessica, the receptionist who dotes on her baby brother, loves to go antiquing, and just came back from her cousin's wedding in Tennessee over the weekend" than it is to think about how to talk to Capital-W Women.
put yourself in positions where you can meet individuals. Volunteer at a shelter, or take a pottery/stained glass/cooking class, or start going to church/synagogue/mosque/etc. Maybe join a professional networking association, or go to hobby conventions. Try to force yourself to be outgoing in other normal life situations - if someone is struggling to get a box off a high shelf at the store, ask if you can help. If you see someone at a cafe reading a book you're interested in (though this is a bit fraught with danger these days), ask if they'd recommend it. If you frequent a particular restaurant or store, notice whether or not you frequently get the same cashier or sales assistant - if so, greet them and maybe make some small talk as you order. This will make you more comfortable with other people and more outgoing, and with any luck at all will spring some friendships or casual acquaintanceships. Some of them might be women in your preferred demographic, but even the ones who aren't have relatives/friends/colleagues of their own. Build your social circle as wide as possible, to net as many contacts as possible.
Be honest if you find someone attractive This one is pretty simple - if you find someone attractive, say so. Obviously not in an inappropriate way ("Hi, you have great tits, what's your name?" is unlikely to work outside of very particular circumstances). Knowing the object of your affection personally will help with this - thoughtful compliments that show that the giver is paying close attention are generally received better than generic ones.
Be Prepared To Accept Rejection This is by far the hardest one - at least for me personally - but I swear to God that if you can somehow trick yourself into a zen-like belief that all the world is an illusion so rejection by a pretty woman is as meaningless and ephemeral as a wisp of smoke from a snuffed candle, you will have a fucking superpower when it comes to dating. Being able to keep your cool, accept "no" as an answer, and roll on, undaunted and unruffled, to the next thing not only makes it way easier to actually shoot your shot, but also makes you better at it because you're not stressing and pressing with the stink of desperation on you.
Alternately you can try the apps - others have left comments with good advice for those, but I retain faith in the old-fashioned way of doing things.
I certainly wish you luck.
I would recommend this, as a test:
Are you willing to endure and sacrifice, for any reason or no good reason, for years, even decades? Can you go years without making a single social blunder? Can you make a million a year...are you on track to do this by age 35? Can you get people to fight for you: would you make a good infantry officer? It's like a modern version of Rudyard Kipling's If.
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