I just walked by and I can vouch that Hillhouse looks like a moonscape for about a 15-foot stretch on the north side of the intersection with Trumbull. The south side of the intersection with Sachem is coming apart as well. While patching would help, it would almost certainly go back to being just as bad by next spring. I wonder if the city could try experimenting with a kind of low-key speed bump at these two locations. For example, they could instruct crews to fill in low spots and then layer on a few more inches of of asphalt to make two raised cushions, about 4–6 inches high, 15–20 feet in length, and spanning the width of the street. They could solve two problems at once by providing a protective cap for the patches and subtle traffic calming at the same time. (At Sachem they would actually have to do two closely spaced cushions to keep from covering up the water main access point).

You can see the situation pretty clearly in the google street view photos:

http://maps.google.com/maps?f=q&source=s_q&hl=en&geocode=&q=Trumbull+St+%26+Hillhouse+Ave,+New+Haven,+CT+06511&sll=37.0625,-95.677068&sspn=49.357162,79.101563&ie=UTF8&ll=41.313709,-72.923545&spn=0.005762,0.009656&z=17&iwloc=A&layer=c&cbll=41.313617,-72.923579&panoid=8USnEs9mk6jTOHxWuWpYQQ&cbp=12,174.99,,0,27.5