Question about gears and hills

[VeloVT]

Also, not to hijack, but have you been fit? If not, it might be worth it to get fit several months before your ride (you want to allow time for your body to adjust and for tweaking). Maybe the seat angle is throwing me off, but the front end set up looks unusual to me. You have an adjustable stem, right? It looks like it's actually a fairly long stem, but the angle is adjusted up very high/with lots of spacers. Is this the best position for you, or was the bike set up more or less like that when you got it? Also, it's hard to tell because the bars (and front wheel) are turned towards the fence a bit, but those bars look really wide and the hoods perhaps a little low. Again hard to tell because of the angle of the picture, but I might consider rotating the bars up a hair as well. Some adjustments in that area might add to your comfort and efficiency.