TL;DR: There is probably some costly problem in your life right now that you are not even aware of. It is not that you are procrastinating on solving it. Rather, this problem has gradually blended into your environment, sinking beneath your conscious awareness to the degree that you fail to recognize it as a problem in the first place.

This post is partially an elaboration on Ugh fields, but there are some decisive differences I want to develop. Let me begin with an anecdote:

For about two years I've had a periodic pain in my right thigh. Gradually, it became worse. At one point I actually had a sort of spasm. Then the pain went away for a few weeks, then it came back, and so forth. All the while I rationalized it as something harmless: "It will probably just go away soon," I would think, or "It only inhibits my mobility sometimes." Occasionally I would consider seeking medical help, but I couldn't muster the energy, as though some activation threshold wasn't being reached. In fact, the very promise that I could get medical help whenever convenient served to further diminish any sense of urgency. Even if the pain was sometimes debilitating, I did not perceive it as a problem needing to be solved. Gradually, I came to view it as just an unfortunate and inevitable part of existence.

Last Monday, after hardly being able to walk due to crippling pain, I finally became aware that "Wow, this really sucks and I should fix it." That evening I finally visited a chiropractor, who proceeded to get medieval on my femur (imagine having a sprained ankle, then imagine a grown man jumping on top of it). Had I classified this as a problem-needing-to-be-solved a few months earlier, my treatment period would probably be days instead of weeks.

Simply, I think this situation is of a more general form:

You have some inefficiency or agitation in your life. This could be solved very easily, but because it is perceived as harmless, no such attempt is made. Over time your tolerance for it increases, even if the problem is worsening (Bonus points for attempts at rationalizing it). This may be due to something like the peak-end rule, as the problem doesn't cause any dramatic peaks that stick out in your memory, just a dull pain underlying your experience. Even if the problem substantially lowers utility, your satisficing lizard brain remains apathetic, until the last moment, when the damage passes a certain threshold and you're jolted into action.

While similar to procrastination and akrasia, this does not involve you going against your better judgement. Instead, you don't have a better judgement, due to the blinding effects of the problem.

Possible Solutions:

I didn't solve my problem in a clever way, but I've begun employing some "early warning" techniques to prevent future incidents. The key is to become aware of the worsening inefficiency before you're forced to resort to damage control.

• Do a daily/weekly/monthly reflection. Just for a few minutes, try writing out in plain text what you currently think of your life and how you're doing. This forces you to articulate your situation in a concrete way, bypassing the shadowy ambiguity of your thoughts. If you find yourself writing things about your life that you did not previously know, keep writing, as you could be uncovering something that you'd been flinching from acknowledging (e.g. "Obligation X isn't as rewarding as I thought it would be"). A more elaborate formulation of this practice can be found here.
• I kind of feel that "mindfulness" has become a mangled buzzword, but the exercises associated with it are quite powerful when applied correctly. I've found that following my breath does indeed induce a certain clarity of mind, where acknowledging problems and shortcomings becomes easier. Using your own thought process as an object of meditation is another excellent method.
• While the previous two examples have been personal activities, other people can also be a valuable resource due to their uncanny ability to be different from you, thus offering multiple perspectives. However, I doubt expensive talk-therapy is necessary; some of my most useful realizations have been from IRC chats.

I want to spend a substantial fraction of my time optimizing myself in the direction of being more attractive to females, and I'd really appreciate your suggestions on how to do so.

Why

It should be pretty self-explanatory, but in case you're wondering: relationships are a big part of personal happiness, and where I am now, I feel more inclined toward increasing the number and variability of short- or middle-term sexual relationships rather than just picking a girl who wants to be my wife and run with it. But at the moment women aren't exactly chasing me down the streets, so I want to offer them a more pleasant experience of my company than what it already is.

Mind-killing

I sincerely think this post should provoke none of the above. I'm not asking for ways to trick women into liking me, nor about gender differences about what males prefer over females, etc. Please try really hard to avoid mind-killing subjects into your comments. I'm 'just' asking for ways to change myself into being a more sexually attractive human being.

Caveat(s)

I'm aware of the dichotomy lying around: attraction can be created vs attraction can only be amplified. In both cases there should be at least something that can be done.
I'm also aware that some people strongly dislike posts full of personal details, so I will try to keep them at minimum, while at the same time trying to provide the necessary description of my situation.

I would like

Try to aim for advice on stable improvements, about aspects that are proven to be sexually attractive to straight females, in the age range of 20 to 40.
For example, I know that height or facial symmetry are proven to result universally attractive, but I cannot really change that, and sole-lifts or make-up are so short-term solutions to border on 'tricking women' (yes, I know that women use those tricks too, I simply would like to invest my time better).

My situation

This is the shortest possible description: I'm a straight male in my thirties, heavily overweight, living in Italy in a 20k people town, with a job paying me about $20k a year.
If you think you need more details ask for them in the comments or PM me.

What I'm already doing/planning to do

The first obvious choice is getting fit, although it's about two years I'm trying different diets with no results, so I'd really need pointers in that direction. I've also heard about training programs that tells you to concentrate on shoulders, because apparently shoulder-to-waist ratio of 1.5 or more is especially attractive.
I've also been told multiple times by multiple sources that women values confidence, competence and leadership. I understand the confidence part in being able to express without embarassment your interest (but still in a socially graceful manner), but I would really like pointers about what area of my life I could engage to become more competent or a leader. In what domains women like competence/leadership?
My only hobby at the moment are the game of Go and dabbing in math/logics/AI, which, as fascinating as they are, are seldom considered very attractive.

What I'm not sure about

Is fashion important? I understand that I need to dress well for my built, but I would like to know if a Versace button down shirt is more attractive than a plain brand one.

False beliefs

Do you think am I doing the right thing? Or am I wrong in my search for attractiveness? Should I concentrate on something totally unrelated? Dose the physical aspect matter or I should concentrate more on character? Am I completely off track?
If you think I'm grossly mistaken, in the name of Omega let me know!

Downvote

If you think this post doesn't belong in a community devoted rationality and self-improvement, feel free to downvote, but at least try to indicate a way to better phrase the problem or point me to another community I can ask the same question.

Thank you very much!