Self-esteem? Tell you what, I started 2 years ago with huffing and puffing for 3 miles one way commute on practically flat which drained me by end of week... (okay, I was really sedentary for over a decade...) I think you are doing much better than me by far I actually really like the profile of your ride. If you sweat, and you will with that hill, you can take shower and have nice beer/water/soda at end of ride at home... no big deal. You probably won't sweat at all going to work no matter the temp... being presentable! I think you got wonderful commute for getting fit, saving time, and manageable as you get better. Pretty soon, you won't be happy with that 5 miles and start figuring detours around to lengthen it

I know you said you didn't want a rack but...assuming you do not have any weird attachment points on the bike for the rack to bolt onto, its only a quick 4 bolts to pop off when you do not want it on there. I just took mine off the old grocery bike in about 2 two minutes the other day bc I was curious to see if I could stick with a cycling group on it. I threw it back on the bike as soon as I got home just as easy

Exactly! The route I've given up which is the shortest distance indeed goes through the Sacred Heart Hospital area. The new route I want to try would be 1.5 mile longer in total but probably be much safer.

Yeah, I should be thankful because the downhill to my work is amazing. Many including you said that things will get better eventually...I decided to believe in that. I also got good advices regarding rack/back and bike setup.

Losing three pounds per week is totally dependent upon your individual physical circumstances. Follow this link for more info:
www.ehow.com/how-5687648-lose-three-pounds-week.html

Hills are the only part of bikeing i hate. My knees hurt so bad going up them and id guess i live in the lowest part of my town so going any where is up hill.then comeing back is much better well for one hill

You mentioned in a couple of posts that you have a mountain bike. Did you ever think of using that for your commute, at least on days when your legs are fried? I have an old hard tail Fuji that I use for my winter commuter. It's a lot slower than my usual commuter, but put it in the granny gear and you can ride it up a wall. It also has the advantage for your self esteem - nobody expects someone to go as fast on a mountain bike.

Any article that parrots nonsense like "muscle weighs more than fat" is worth ignoring. I'd recommend the OP shoot for 2lbs/week -- it takes longer, but is much less likely to throw the metabolism out of wack, and will be an easier transition to the "maintenance" phase of dieting.

Just climb that hill and focus on eating veggies instead of sugar and white starch junk. You'll lose weight.

That article seems fine as far as it goes, but it doesn't give any special insight into losing 3 pounds per week vs 1 or 2. I didn't say it wasn't possible, just that it isn't easy and perhaps isn't healthy (according to some sources). Just to throw out some numbers, if the OP's maintenance calorie intake is 3,000 calories per day, he would have to cut it to 1,500 per day, which many people would find to be a hardship. The exercise helps, of course, but a 9-mile round trip would burn maybe 350 calories, and he's not doing it most days. (Although maybe he can fit in daily exercise some other way).

You're correct that losing weight would help the OP get up the hill. I'm all for losing weight (I'm doing it myself). I just think people should have realistic expectations of how fast they can accomplish it, so they don't get discouraged when it doesn't happen that quickly.

I wish i could have steep climbs like that on my commuting.

Agreed!

Where I live, the town Is a Hill.. now I live near the Bayshore, near sealevel.
earlier address I got off and walked a couple blocks,
still do when I visit friends living up by the ridge line.

The half commute seems a sensible option. It took me over 6 months of commuting to be able to ride my full daily commute (20+mi, 1000+ft per day, combined). I rode the shortened version (7 mi and maybe 3-400ft?) for a long time, and still do occasionally if I'm not feeling up to it.

Don't worry about going slowly - every day you ride is an accomplishment!