I have more time in singles than twins, but have kind of worked my way up and feel there's a place for each. I have to say, when flying passengers over water, mountains, at night and low IMC, I'll take the twin. When one does a lot of cross country flying, they will most certainly encounter more challenging weather conditions and those conditions will change along the route. There are also times I will depart in a twin where I just wouldn't in a single. Last year after skiing, we left Denver (BJC) with about a mile of visibility, blowing snow, low ceilings with tops at FL230. Tower asked us to tell them when we were positioned on the runway because they couldn't see us. Of course, this is in a KA which is a K-ice, pressurized turbine twin. Needless to say, I wouldn't have departed in the TN A-36 I used to fly and not in the P-Baron I flew up until two years ago. In the KA, we didn't have any issues. Cycled the boots twice on the way to FL230 and were on top from then in. I'm not saying it wasn't a challenge and we didn't do a lot of planning, but once we saw we could get above icing levels and there were no other reports of icing in the climb, we departed. I had a very capable right seater with me.
Best,
Dave