My son lives in Colorado Springs and needs a used, affordable all-wheel drive car (price up to 4,500 USD) which will safely get him through the next 2 winters.
The difference in asking price from local dealers is about 1,000 USD.
Any advice on cost of repairs, durability?
It’s a coin flip when you’re talking about 10-12 year old vehicles. Both could be fine or both could be junk; no one knows. Any used car should be inspected. Failure to do that means relying on the automotive gods being on his side.
Why not get something like a Blazer. It’s more common, parts and repairs are on average cheaper, and you don’t have to mess with annoying, expensive timing belt replacements and in the case of Subaru; a fairly strong possibility of head gasket or transmission problems if it has an automatic.
Put “winter tires” on a front wheel drive car. The AWD cars will cost you dearly in expensive repair bills. You can expect to pay $4,000 on the Volvo over the two years. If you have to choose between these two cars, go with the Subaru.
If the Subaru Legacy has a 2.2L engine go for the Subaru after a mechanic blessing. This is a very reliable Subaru engine. However the 2.5L is likely to blow the head gasket and I would avoid any Subaru with the 2.5L years 1996-2004. It is a very common post on this board and a very expensive repair.
based on my study about Volvo 1999 S70, it has been proven as a good durable car and has the chances of having it withstand the toughness of other cars. Some Volvo repair questions are very open for review to prove this to you. it is a good car choose between the two.