One of the major disadvantages of me retiring early and moving to Hawaii, is my opportunities for meeting woman my age, (I meet lots of sweet 70+ old woman) is really limited. I've been pretty happy with online dating services, although I have been procrastinating about getting serious about using them again. I've met 3 serious girlfriends online, even if they have not turned into
THE ONE
I think Shawn's advice was excellent. I think match.com is the best primarily because its the biggest. I personally hated the heavily promoted eharmony, but I know enough people that really liked it, that it maybe worth a shot of you get fed up with match.com. Eharmony is significantly different than the other sites because they do the searching for you as advertised. The free ones (with possible exception of yahoo) are worth what you pay for them.
I like your phrasing for financial responsibility, and lets face it LBYM for most people means "Beyond" your means not below. It is deal breaker for me also.
My experience is that generally the woman that I've enjoyed email/flirting with online I like best when I meet them face to face. However, there have been plenty of counter example, girls I've spent two months emailing and then found zero chemistry after meeting, or the opposite; exchanged an email or two meet a couple of days later and we hit it off. Good writers, like yourself, who are comfortable discussing things with strangers over the Internet, have advantage compared to most people on the Internet. Your writing can create an aura of mystery/excitement which can help spark interest when you meet face to face. So don't be in a huge hurry to meet face to face. On the other hand waiting too long is a waste of time and can great false expectations.
This is a personal fetish of mine but I HATE MEETING FOR COFFEE. Partly cause I am not much of a coffee guy, I don't care for hanging at Starbucks. But primarily, I think it sends out the message, "I am kinda of interested in you but not enough to committed to wasting a whole hour or more getting to know you." Ask him to lunch, dinner, a walk, the zoo, or if you have a shared activity, e.g. art museums, tennis, spots teams, attending lecture at the university do one of those things.
Finally, the whole etiquette about who pays is ridiculously complicated. However, if a girl ask me out I expect her to at least offer to pay. (The only one I let pay was a doctor in mangement.)
Of course, if I was really good at this dating business, I'd have three 25 year olds like Hugh Hefner