I can do that, right?

The T had a pretty lousy winter.  They have faced up to it (at least somewhat) and are doing track improvements and such as part of the cleverly named Winter Resiliency Improvement Program.  I have been thinking about what a home WRIP would involve.  We were lucky last year.  There were big icicles from the gutters, but we seem to have avoided the ice dams.  Our attic insulation is good.  I booked an appointment with the roofer to come and do an inspection of the shingles, but nobody showed up.  The office person was confused, but couldn't explain why we were skiipped. I was peeved, and didn't re-schedule.  I will get the gutters cleaned, though.  A lot of snow moving happened last year.  I expect it would be easier if the sidewalk and driveway were smooth instead of cracked (in the case of the sidewalks, the cracks have grass growing through).  There is one depression (pothole?  sinkhole?) in the driveway.  I have looked up online instructions about how to fill holes in asphalt.  It seems to me that I could do it, although the best thing might be guys (probably) with a backhoe and a steamroller. Not going to do that.  We were standing in the yard once when a guy in a truck going down the street suggested that we hire him to resurface the driveway.  We declined.
In other winter is coming prep, I'm considering trying to make this hat, from the Geek Knits book (photo by Kyle Cassidy).

It is another project for which I don't have the required skills.  The knitting group members, who know how much I am struggling with a small sampler of stitches, pretty much gave me the side-eye when I mentioned it.   Probably what I need is a driveway group, in which the members are supportive but will give me practical feedback about what I can't do in that regard.
PS I have been wishing for the skills to make Maddie's Mittens (named for the character in eegatland's books)
http://www.elizabethwein.com/blog/maddies-mittens
Those are clearly way too hard for me.  Fortunately, I already have other hats and mittens.