nah im in orlando which is a transient city... majority are theme park workers with little ambition and the ones who do have it don't stay long. only women i met with money are tourists...
The paying for dates thing is going to come down to personal/cultural value systems and ethos, once you have cleared the demo that really
can't afford to pay for their meal, there plenty of women who make a few 100k a year, and more and would not be happy paying for a date. It's a system. And there's also many women who make the same as you, who are happy to pay or split. I met someone this year who I asked out, and she was RETIRED at like 40 years old. Probably at least 5m.
You can't control your class/wealth/where you were born, Here's what you can control, where you spend time, and how you carry yourself. Get comfortable in those kinds of places, upscale spots, until you really are comfortable. Roll solo or with a like minded friend. Actually enjoy being there, so it feels natural. Skip the club and go to the bar at the 4 Seasons. Or the St Regis. Skip the local bar, and go to the latest hot restaraunt. Get out of your comfort zone and keep pushing it. Take a sincere interest in people.
don't know Orlando at all, start hanging in those places, and it will open up a lot for you, but it has to be authentic. And if you can, hang in Lauderdale, or Miami. Social circles and opportunity will start to rise. This is like the hard way, but the way where you actually grow as a person. The easy way is ID a few spots where rich women hang out, and just roll in weekly, it will happen sooner or later.