I had that problem of having hills inconveniently coincide with run periods when following run/walk training schedules. I would turn around and go back for a bit, or do an out and back on a side street to avoid it. The time I didn't, and ran whatever came my way, which included some decent uphill sections, I was very happy with myself. But in the last minute of the prescribed 6 miles, I injured my Achilles and it's taking months to heal! Of course, in looking at my log, I had been ignoring heel pain or treating it as PF, given my history of that, so several lessons there for me, but not necessarily for you!
I figure I might as well do them when they come up, as I can't avoid them or just turn around in the middle of a race or course ;-) just seems like they never hit during a walk. I can avoid them entirely by just going to one of the rail trails, and sometimes do.
I've ended up with shin splints, PF, and sciatica in the past few years all when ramping up training. I'm taking it so very slowly this time, but with daylight in the evenings finally coming I'll be doing more starting soon.
If I was training for a race with significant hills, I would do them, but I have a lot of hills in my area, so I try to avoid the steeper ones unless I have a good reason to run them. For the six weeks of Couch to Half Marathon that I managed before getting injured, I did the two shorter runs per week in the early mornings, so I went up and down my street, one out and back being a half mile. There's a hill at both ends, and one on the connecting street, so I just ran them if that's when the run interval started - which seemed to always be the case! It is weird how that seems to happen!
Your slower build up sounds like a smart plan. Good luck!