Converting Money into Girls, if your not willing to engage professionals, is not as easy as you'd imagine. Or rather, it is about as hard as you'd imagine. Money doesn't make that big a difference.
Investing in some salsa/merengue lessons is a pretty good way to go. It worked well for me in that it's a very non-geeky thing that lots of girls like. It's also a fun environment - in the right places, you can dance with lots of people without it being a Big Deal asking someone to dance.
No way. It may not be as easy as people make it seem, but if you take care of yourself, and dress really well (I'm talking Armani, etc) there is no way it's not easier. Personality is still a factor, but money gets you in the door.