Interesting post. I was planning Ostend the weekend before last and I mean PLAN.
Making such trips in different seasons throws many variables into the equation. In summertime, my attitude to the trip is totally different to making the same trip at this time of the year. When you know you can survive for a few hours in our coastal waters - assumimg you survive the ditching, a lot of the anxiety is removed.
This time of the year, I would not count one's chances too highly unless you came down very close to passing shipping. I tend to cross at a minimum of Fl 6,0 - that gives me thinking time, glide distance and the chance to use R/T and look for the "target" ship - let alone maybe some problem solving time.
I think as you point out, it all depends where the icing layer is and can you remain clear of controlled airspace in clear air above to give you sufficient time to think.
I think the only other real concern about being in a single is at night, particularly when departing an airfield in a built up area - that makes me think! But hey, we still get out of bed most mornings.............and when did you last risk assess that!