IMHO, lawyers, doctors, bankers, and recent Lotto winners.... are the only dudes who can seriously entertain scooping up one of these chicks.
Unless you have the resources, I would suggest just being her favorite customer and visiting her regularly at her job.
If you want a better session than the one you can get at the house, see her regularly and then on your B-day bring a lot of extra cash, maybe even do an outcall with her at your favorite hotel or house.
There are some really nice girls out there and if you could erase their financial burdens you could hit the jackpot- keep in mind, the vast majority of these girls need much better coping skills and a many hours of psychotherapy. Sounds appealing now?
My 2 cents....
TB