But there are plenty who have very capable Permit aircraft which could easily be well enough equipped to fly through a cloud layer in uncontrolled airspace, or at night.
I agree, of course.
I suspect that the first half (IMC enroute) is moot because you will never get caught
Just look at the vast numbers of plastic planes coming out of say the Czech Rep, with what is basically IFR avionics. I think some can even fly an ILS though that is likely to draw attention
There is no prize for guessing what kind of use some of these well equipped machines get put to.
The other half (night) remains a problem because it is rather obvious in the breach and would draw attention.... however, in the regulatory sense, this one (night VMC) is more likely to be permitted. VFR-only helicopters already fly openly at night in the UK and elsewhere.