So I picked up my new bike (first bike in 10 years) yesterday and rode it home. This is about a 1.7mile trip so not a huge deal. This wen pretty smoothly except 1 hill that I just couldn't do (at least in traffic) so I walked in up the sidewalk. The rest of the trip wasn't too bad. I decided to go on another ride yesterday afternoon, which presented a few more challenges. The trail around the park is a couple of miles and has a couple of longer low grade climbs which I thought were going to kill me to the point that I walked my bike because my legs just above my knees were buring a lot. I went for another ride around my neighborhood this morning, which wasn't so bad except that I worked to make sure that I was staying away from any longer climbs. SO here are my questions...

1) When you started riding how in/out of shape were you? I am pretty out of shape as is evidenced above.
Very Out of Shape.
2) How many miles did you start out riding at first? How often?
I think I made it a mile with a small hill of about 80' elevation
3) I know that hills are never "easy" but when do they become less daunting?
In the words of Stormcrowe, they never get easier, you just get faster
4) When did you feel comfortable at any sort of speed? Right now if I am headed down hill and pick up too much speed it kind of starts to freak me out.
I've ridden over 500 miles this year and I still get freaked out when I go over 30 mphs.