You're welcome! I'm happy to try to help. I know how frustrating online dating can be, believe me!
As far as first date ideas, you have some good starts there...just expand on them. For example, what attractions in the city? Maybe you could be more specific. As for the waterfront, what kinds of things could you do there? Get an ice cream? Have a picnic? Those would sound much more interesting than just a walk. Or you could check out some of the date ideas on Ask Dan & Jennifer like
300 Fun & Creative Date Ideas.
As far as humor goes, if that's not something that comes naturally to you, then maybe it wouldn't be the best choice. You don't want to come off like you're trying too hard. Just be you and try to let some of your personality shine through. Be friendly and approachable. The 3rd email you listed is a good start. Say hello. Ask how she is. Rather than asking where she thinks she might go next, ask what her favorite vacation or destination was. Mention someplace you have been and tell her what you enjoyed about it. But don't make it too long. Women don't want to read a book. Tell her you hope she is having a fabulous day.
Dan & Jenn also have some pretty fabulous videos about emailing and approaching women on online dating sites you might want to check out if you haven't already.