Not sure if this is any help but my street in east rock (a subdivision in new haven right outside of Yale) always has plenty of street parking and it’s free. I’ve left my car here two weeks at a time and the only issue was when they did street cleaning for all the leaves in the fall. Super safe, no accidents or breakins or anything

It’s about a 12 min Uber to the airport. If you’re interested you can DM me and I’ll tell you the roads that I know for sure have available and free parking