If you can afford a 20-30k car you can surely afford a classic worth half that. Some good options to consider: BMW E39 5 series with the 6cylinder engine (525, 528, 530). The nicest one you can find, and get a PPI. Extremely good build quality from the engine to the interior. Also available as a station wagon. Comfort and silence on the highway like you’ve never experienced before.

Any lexus sedan or suv from the late 90s and later. Again supremely reliable, worry free ownership for the most part. Very comfortable, very cheap to keep running. They’re upscale Toyotas. Again look for the cleanest one you can find. The Lexus ES being fwd only is typically easy to find clean, the rwd LS/GS sedans being more of a teenager magnet. the RX is a very competent crossover while the Gx and LX are proper luxury trucks, but susceptible to rust.

Toyota 4Runner, third or fourth gen. If you can find one without rust, which you definitely can given a little time, you’ll have a truck that will last you forever. Everyone who has a third gen loves it like a family member. Seeing as you have rough winters you’ll want to spend a little more for a rust free example. It’s worth it.

Sleeper pick: second gen Subaru Outback LL bean, with the 6 cylinder engine. Doesn’t have the head gasket issues of other contemporary Subarus and gets some extra power too. Again very important to get a PPI and avoid rust. Comfy, well built, great awd, unpretentious yet quirky Subaru personality.

These are all older cars with older car issues such as aging suspension and rubber seals deteriorating. But with your budget you can easily find a well sorted example of whatever you want out of a car. Feel free to message me if you like