As an ugly guy, I suggest a holistic approach. Go to a place where your money has more value, and where your social standing has more value.
Compromise in areas that are less important to you, regarding females.
From that place of optimizing your position and focusing on your prime needs and desires, practice your social skills over and over until you are those skills – in a unique and comfortable and intriguing way. Be interesting, even to yourself.
Having good skills in a poor environment is not as advantageous as poor skills in an advantageous environment. Going after a woman in all ways above your station is not as advantageous as going after a woman above some of your station and below other aspects of your station. Know what to choose, and what to give up.
And then being ugly is fuglin fun. You can in some cases do far better than handsome young guys. Providing you can fuck like hell.