Between the wife and I we've bought a bunch of cars over the years ranging from new to 20+ year old classics. The most pleasant experiences were when I knew in advance what specific vehicle I wanted and what I wanted to pay, lined up everything in advance on the phone, and only had to show up to sign the paperwork pick up the vehicle and leave. Never buy new if being efficient with your money is top priority. It's always a bad deal in that sense. If you simply want something new, or want to have something for perhaps a little longer without having to fuss with replacement/etc, that's a better reason.
I trust car dealers about as much as I trust snakes except snakes are more straightforward about their intent. Over-prepare. If at all possible show up with your own financing (or better yet, straight up cash in the bank) in advance. They'll inevitably try to rake you over the coals if you use dealer financing regardless of whether you buy new or used. Be ready--and more importantly, willing--to walk out if you can't get a deal you find acceptable. A customer being pressured into a questionable sale because he/she doesn't want to walk out is the number one reason people end up with bad deals.
You can't outright expect any vehicle to last 250K without stuff breaking along the way, especially if you're talking about stop-and-start daily driving (not all miles are alike) and the car getting beat up in the manner that family cars usually do. Winter and children beat cars to hell and it sounds like you have both of those things. A reasonable number of vehicles reach that these days, but that's still a bit of reach as a straight-up expectation. You want longevity with low maintenance, then what you want is simplicity for the best chance of success. Avoid turbos or CVTs. Definitely avoid any model that's in the first year of a new revision. Watch out for small little engines that demand 20 weight synthetic oil. We live in the era of 100 dollar oil changes, and it's dumb.
I'm not enthralled with all-wheel-drive. All cars are AWD for braking and it quite often gives drivers a false sense of security in poor conditions. It can be nice to have for crawling a steep icy driveway or some such but it doesn't replace proper driving technique for the road conditions. If you can fit it in your budget, good, but I'd rather have a nicer 2WD car than an AWD sardine can. Subaru has good AWD setups and a lot of experience with manufacturing them.
If you aren't already familiar with a car, try to get familiar with it before you buy. A lot of modern cars are built with a bunch of gee-whiz features to try to win people over at first glance on a showroom but which aren't always necessary or well-thought-out in actual use. Navigation systems with poor button layouts or excessively complicated menus are a common culprit these days. If you're regularly hauling around a bunch of kids and doing normal family-type chores a minivan might be worth a look in addition to the classes you mentioned above. Maybe they aren't "cool" but that's the job they're meant for and they do it exceptionally well.
Danth
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