I would suggest, as others have, to just relax a bit. Don't put too much pressure on yourself. When you do ask her out, mention some things you like about her, such as "I like the way you're so patient with the youth group kids, and how kind you are to newcomers." Let her know that something real has caught your attention.
The Valentine's Day thing... That's a tough call. Some women would think it was sweet, some would probably think it was a bit much if they didn't quite have the same feelings for the guy. If you're really hesitant to ask her out directly, you could maybe get a lighthearted Valentine's Day card and give it to her. Her reaction to the card might give you a hint about her feelings and you could ask her out if she seems happy or interested.
The money thing... as long as the money problem isn't evidence of something greater (I'm talking gambling debt, etc) then it really shouldn't be a problem, IMO. Some of my favorite people in the entire world are flat broke. Besides, it will be a while before you have to worry about being a provider for this lady, even if you two do hit it off. You have time to get back on your feet, and hopefully she will be more concerned about your heart. If she's looking at your wallet first, you probably don't want a relationship with her after all.