I don't know many Hobbyist in Philly, but I can speak for myself and maybe I can represent a portion of the PA gentlemen.
I've had a few "fantasy dates", they're expensive and usually reserved for out of town travel. I save six months for two a year. I wrote a story about one on the Vegas board. The link is below.
For the local dates I scrounge the cash by part time tutoring, saving half my lunch money, scooping up all the rebates, refunds and random check that come in the mail and fathers day / birthday / Xmas gifts.
I am middle management, recently retired, It takes me about two months to save $350. Over Xmas I can spend a little more.
So to answer your questions more directly:
We are not new York or Washington, we don't have wall street or the nations capital to bolster our client base, but we are a nice city, with a neighborhood feel, that's big but not crowded, rich in culture, but not over the top. We can be upscale and elegant and down and dirty all at the same time with the same people on most days. So stop and enjoy Philadelphia. Take some time to check out the constitution center, the historical sites and the museums. Catch a show on south broad and stop for a cheese steak in south Philly.
Develop a client base over time. Start by offering some "get to know you" specials.
Regarding the "pre"-s. I like to pre- book, but I seem to get jammed for time a lot between work and family so I also seek a fair amount of last minute dates. But I could pre-book a Xmas, fathers day or birthday date.
Pre-paying and deposits are tough, I've tried it three times and got ripped each time.
Do you do lay aways? Maybe a Xmas savings plan?
With a coupon book?