Is your issue more about twin v single rather than flying above cloud per se? If you have IR capability and the engine fails in a single, can the IR capability help much unless you are fortunate enough to be in range of a suitable place to land with instrument guidance?
Flying is all about having " outs" otherwise you are into Russian roulette flying
I don't trust Piston engines as much as some do but its not just engine failure there are multiple other reasons why you maybe forced to land en route.
I would be reasonably happy in a Cirrus with its reliable BRS as that would give me the out I want
Single turbine? much less likely to fail so more comfortable
Piston Twin they will happily fly level on one all day so again reasonably happy
As posted above with an IR you stand a far better chance of landing with engine or other problems with full instrument flying capability even if the base is 200
No instrument ability and even the let down through cloud poses a serious threat
Pace