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From a strictly financial standpoint, you are far better off keeping the Subaru until it is 10+ years old. All the money you don't spend on payments can be used for lots of fun things. I keep all my vehicles for at least 10 years and this has allowed me to accumulate enough money to pay for the next new vehicle with cash. This changes everything including buying my wife a Volvo that cost 2X my TC. So I'm not opposed to luxury or having nice things. But I still love my TC. But if you NEED a TC because of it's utility or the Subaru is rapidly failing, then you can't go wrong with one priced in the mid 30s. This assumes you pay it off and drive in several years beyond that. Resale value stops becoming a significant issue once a vehicle hits the $10,000 (approx) resale price point. At that point there is not much variation in price and you have extracted the most value out of the vehicle. Resale value only matters for those who are flipping cars in after 3-6 years of ownership or those who overpayed for the flavor of the day. I owned a 2002 Forester that a sold in 2016 for my TC. I have never missed the Forester....not even the 4WD. But I live where you have to travel to get to the snow.

Snow driving is fine but only with actual winter tires (mandatory over here). Not all seasons or all weathers.

It's based on the Focus and most parts are shared. Don't worry about it.

That would be my concern in a snow area. I don't have snow where I live. The Transit Connect is good enough in the rain. Someone else could weigh in on how they have driven in the snow. For me, the Transit Connect is not luxury and comfort. It does not offer luxury. It's more of a vehicle which does the job. I have seating for 7. There's a lot of space. The seats fold down for the occasional trip to Home Depot or Ikea. Everyone can get in with their book bags, sports equipment, groceries, etc. The ride is bumpy. There is some road noise. The HVAC system is loud when you're trying to blow more heat or air conditioning.