Hi, Jswann... Hope you find some good advice here, as there are many who active riders and buyers.
I live in Florida but used to live in a hilly area of CT so I know what you mean... I can't imagine buying an electric bike without road testing it.. Ebikes are expensive and it's new to you.
Knowing what I know now, if I were in your position and you weren't that restrained on budget, and you like your Trek (good bike), I'd buy a reliable conversion kit from a domestic supplier. They can walk you through the purchase and provide good customer service, even if you have someone install the kit for your.
You'll end up paying around $1500 for the complete kit, plus installation cost, around $150. This kit would take you up any hill in your area (assuming youre not climbing Mt Washinton, or Pikes Peak!), and give you great range.
Buy a direct drive motor , either Crystalyte or MagicPie II... These motors have been around for years and people have put tens of thousands of miles on them. Downside it that they are heavier than other brands.
Buy a lot more battery than people tell you.. Hills chew up battery energy big time. 36v20ah minimum, imo.
Get something that has regen so your downhills can charge your batteries a little.
Try to buy something with peddle assist.
Or the Bionx kit is very popular, also around for years. Around $1700.
http://www.biketechshop.com here are some reviews on them
http://electricbikereview.com/category/bionx/
You could start by calling the guys and girls at ElectricRider.com. They always answer the phone, they have been around for at least 5 years, and they have a great selection.. Not cheap, but nothing worthwhile is, IMO.
http://www.electricrider.com