Yes, you do have some pretty challenging hills out your way. What kind of gears are you using on your current bike? Having a hill climb gear that's so easy that you seldom or never use it isn't a problem. Not being able to grind up a hill is a different story. What other people do or ride with doesn't matter. You're the only person that bike has to make happy. If it takes a triple for you to master the hills in your neighborhood - so be it.

Honestly, that's the kind of question/service that I think a good LBS should help you with. Are you working with the folks at Scenic Cycle? It's been awhile since I've talked with them but they're good people.