I think it's so great you're doing this! Great job fighting that uphill battle (literally). Terrain like that can be so tough. I mostly run on a treadmill since I'm waiting for the weather to get better, but I did one workout on my road and the hills were a killer. I hated running into the wind too, when I was already started I realized I should have put something on to cover my ears.
Keep up the good work! Good idea stretching the program out, I had to retry a day of week 2 twice and got stuck again on week 6. I'm about to start week 7, it's hard but worth it! Try not to be negative while running- tell yourself, I can do it!! Just a little longer!! Don't quit!! Good music definitely helps motivate me too