here are situations I see women who fit my type
working out at a gym with headphones on - super hard to make anything happen
working at various locations - obviously impossible
at bars/clubs with 4 friends- approaching 4 random women is super awkward and uncomfortable and difficult
at the mall shopping - WTF do you say? nice shoes?
I get ZERO natural dating opportunities with anybody decent
When i do sometimes talk to women at bars/clubs, they usually like me but those are the more average ones or they are very cute but 34 to 38 years old or they're single moms which is why they put in effort to make it easy. The good looking quality ones are clearly not interested in meeting anybody so they make it impossible to approach them.
Start going to yoga or a ballroom dancing, idk, just practice doing that stuff you think is terrifying.
You are focusing on everything that does not really matter, and writing off doing the actual one thing that will help you get closer to what you want and that's approaching women in public.
Just go up to women at the mall and say "hey I saw you from over there (point in the direction) and I though you looked interesting / gorgeous / whatever" it doesn't matter to much what you say but how you say it. Someone posted a video for day game for beginners yesterday, watch it and do that.
You're only issue is not your money, looks, or any of that. It's that you dont want to approach the women you really want. You need to just do it. Forget about your picture or clothes or job. This is the number one thing holding you back, not the stuff you make threads about.