Light aircraft that can operate in most winter conditions are pretty few on the ground. As others have said you need to make sensible decisions about the weather and the ability to climb on top.
I can think of very few in line aircraft. The Mooney of course and the Cessna Skymaster with boots are very good examples.
The vast majority of twins use boots - I can only think of the DA42 that uses TKS which in my limited experience works ok.
For a host of reasons I am not convinced these aircraft are really at home in the weather in winter which would ensure reliable capability - for that I think you probably need to step up to something like an Aztec, which whilst old, I think is a super aircraft able to provide very reliable point to point transport with comfort even in conditions that would be unpleasant in "lesser" aircraft.
In anything "lesser" the key is to ensure you are always ahead of the weather rather than being able to rely on the aircraft to "cope" with it.