You are a capable pilot but general aviation is a different world than what we have done in the mil. Small GA aircraft on a budget don't generally do well in conditions that make a great ski vacation. There is a reason why GA pilots generally fly in fair weather...its more about aircraft limitation than pilot skill. If you don't have a high performance aircraft with TKS you will need the flexibility to shorten or extend your trips to accommodate the weather. My biggest fears as a GA pilot is traffic and icing.

Look into Mooneys, Bonanza etc for trips to the Bahamas and Orlando and buy a Subaru for skiing...

Another airplane for your list would be an Aztec. Similar to your choices, but it will carry its own weight (more that any of the other choices at approx 2600 lbs) and climb out on a single engine. It goes slower but doesn't seem to pick up as much ice as a Baron (my totally non scientific observation) but it will cost more in gas. The engines are mostly bullet proof, and no turbos to worry about. They are going ridiculously cheap right now because as another poster said, feeding and caring for 2 engines is much more than for one. More than double, which doesn't seem to make sense. Good hunting!

Geronimo conversion of the apache is also very capable. Good (maybe 400-500 from) single engine climb rate even at max gross.

At sea level.

The apache is slow, with the Geronimo marginally faster (140 kts). They're also old and bring with them a host of issues associated with their age.

I've never worked on any of the Piper indian twins that didn't have a plethora of screws that were the wrong type and size, and owners seem to have a fondnesss for driving PK screws into nutplates and the use of rivnuts, things which make any mechanic tear their hair out and drive up the maintenance costs when doing inspections or simple maintenance.

The apache, the basic airplane before the Geronimo conversion, doesn't actually have a positive rate of climb; when one engine fails, particularly on takeoff, retarding the other is often the appropriate course. Either way, selecting a place to put the airplane on the ground after takeoff, instead of planning a return to the airport, is a very likely outcome.

Experience that in the mountains on a ski trip, and your only choice will be off-field.

Navajo is excellent with ice, at least much better than many singles and twins (better than Caravans).

Why are you ruling out singles like the Cirrus?

I had a 310 for a couple years, swear Ill never buy another airplane with 24 plugs and 4 mags! And I have my A&P.

I'd look at the 300hp Cherokee 6 or Lance. These are good platforms that can carry a family and lots of gear without the expense and complexity of two engines.
I could get the 310 down to 18 GPH just putting around but I think I planned it around 23-24 if I wanted to get somewhere. Look out for wing spar corrosion and prop AD's on the older 310's.
Use the airlines when the WX is carp.

You guys are posting some great advice. Thank you to everyone!!

Side Note -- There is no particular reason I was starting at twins. Just a single engine guys perspective of having redundancy. BUT, like everyone seems to be mentioning the maintenance and upkeep costs may make it preventive. I believe someone mentioned a Cirrus, Cherokee 6 or Lance so I'll take a look at those as well.

Add the A36 Bonanza to the research list too.

I was in the market for a four place single several years ago. As you did, I started to look at light twins. I bought an Apache with new motors and props. The price we settled on was in the mid 30 thousand. My aircraft is STCed auto gas, and burns at cruise 16 to 17 an hour, my best is 15 an hour. I routinely cruise at 11.5 and 10.5 depending on which way I am going. The aircraft is extremely stable on an ILS approach. My single engine performance: At gross I can hold altitude at 5,000 MSL 100 mph. I also fly over a lot of open water, nothing beats the feeling of a second engine purring along when your family is with you. I do a lot of my own maintenance and agree if you can't do most of it yourself it can get expensive, but it is not difficult. I highly recommend a twin engine aircraft.