I was at HQM on August 15th, in my C-172S
I was there roughly noon to 3p.m. (I'll check my logs later to find out exactly), and here's what I recall about it.
The clouds were OVC at 500ft., the layer was solid, but quite thin (less than 100 ft.), at least during the time I was there.
Most importantly, the cloud-line STOPPED right at the airport. Everything to the West was 100% OVC, and everything to the East was 100% clear.
As the cloud-line shifted a little bit, the airport was going in and out of IMC conditions.
IMC briefly as the clouds advanced, then VFR again as the clouds retreated.
Some of the planes I was with did depart HQM, quite literally to "look for VFR" at other nearby airports.
We wanted to go elsewhere, but other airports were sadly socked in.
We were careful to depart VFR from HQM, sometimes waiting for the clouds to retreat again.
(no one in my group had a twin engine, and I didn't see any arrive or depart while I was there)
I am not an IFR pilot, and know very little about IFR rules, but as I understand the VFR rules
at an uncontrolled, class-E to the Surface airport, when we judge that clouds and visibility exceed minimums,
(using all available AWOS, ASOS, and your own eyes), then we are free to take the runway with standard CTAF calls.
You might be misinterpreting what the pilot meant by "looking for VFR".
Within the context of my fellow pilots, we were departing VFR,
and looking to see the conditions at other nearby airports (W04 and S16).
If the pilot judged it was VFR, (and it was on-and-off throughout the day on Sunday), I think he was both legal and safe to take-off.