Update (in case anyone in similar boat is looking for motivation like I was before I started.)
I'm still at it. Went on vacation a few weeks right after I started, but I kept at it when I came back. I feared I might have to start from square one but I was suprised to pickup right where I left off if not even better.
The hills are still the tough part but they don't discourage me or anything. They're just there. Actually, if anything I'm looking forward to getting better at them and tackling more rides with them rather than avoid them in the future. Weird.
I was interested in if I was being a baby about how steep the one hill was and did some rough guesstimates of the % grade of the hill (after looking up on line how to calculate.) I figured the length of hill from the gradual start to the crest at about 3/4 mile with a elevation gain of about 350 ft. That put the grade around 9% if did everything right. From what I read that is nothing to sneeze at. It takes me a couple 1 minute stopping breaks to refresh before continuing to ride up (more like wobble up) in lowest gear.
Only change to bike was to add a trunk bag. It's nice and convenient to just toss my keys, wallet, and phone in there instead of dealing with them in my pockets. I think the bike is working out fine but I can't help but lust after something new and shiny. I'm thinking maybe a touring bike or cyclcross like a surly cross check might be what I get next. Something that I can still commute on but also something that wouldn't be bad for a little distance riding on the weekends.
Until next time.