A Car for Humans That Isn't Soul Crushing

I went and got a Merc for many of the reasons you call out. Fun safe car. Test drive something that has 550 and formatic on it. An E class should be able to handel the kid seats. Get an S class and the back seat is huge!!  On the other side of things there is the GL and GLS suv things. My wife has been eyeing a GLS550 and I test drove one hoping I would not like it. Ya I want one.  My only advise on these is get one newer than 2010 m. Post 2012 cars are even better and most will have had a refresh making them look very much like the current cars. Like every car a service history is a must if you want reliability.  The poor quality of the early 2000s has led the a steep depreciation curve of these cars but Mercedes fixed this when the divorced Chrysler and stoped making cars to a price point and returned to making cars to a quality standard. 
 

Steve said:

But is it a sexy red wedge that stands out from the crowd? No. It is not. And that makes me a little sad.

This is a key point.  If what you really want is something that looks/feels sporty and sexy then your only option is to work towards a situation that allows something sporty and sexy.  If you really want it there's always a way to make it work somehow, there HAS to be a way because the alternative is to accept being unhappy.  That should never be one of the options.

From a different point of view, my wife and I have always had his/her Foresters for daily use and a Eurovan for weekends/trips.  Hers is an 07 XT Sports and she actually isn't crazy about the attention it gets from random people when she's out and about.  But it gets winter/summer tires per season and it works well for her and our (now) 6 yr old during the day.  Mine is a 98 body, 05 STI under the skin, turbo from an Indycar, '15 STI steering rack, big Wilwood brakes sized to fit inside 15" wheels with 205/70 tires.  Everything lives outside year round in the midwest.  My concession to high performance is that if it's below 0 deg I'll let mine warm up for a while before driving off (also to get some heat going).

The big difference is that mine is specifically made not to look sexy or sporty.  It's rusty, it has a big dent on the rear from a hard snowbank (almost had it!), lots of small dents from commuting (as much as possible) on Michigan gravel roads.  The paint is peeling in spots.  Casual observers and most 'enthusiasts' never give it a 2nd glance.  Only builders or racers have ever been interested in it.  But that's the way I want it.  It makes a little less than 400hp at the wheel, I get usable torque from about 2800 rpm, it's set up tail happy and the handbrake shoes have been relined with an aggressive high temp friction compound.  Which lets me have a little fun to/from work, which makes for a better day overall.

I do sometimes miss having more 'showy' cars, but I don't miss feeling the need to 'preserve' something as compared to enjoying it. 

I actually read your post last night and it resonated a lot with me. If the question is: "how can I get something as that brings me as much visceral joy as my AW11" there answer is nothing, because your connection to that car is much greater than the actual sum of its parts. If the question is "how can I get something that I enjoy driving that can also reasonably transport a family" the answer is: lots. 

If I were in your shoes my choices would be between:

E39 M5

V1 CTS-V

1st gen Cayenne

Steve, I'm notoriously cheap which is why I like the idea of driving a mundane  / practical car every day but having a play car(s) for the weekend.

A friend had a sticker that said I drive a beater during the week so I can race a beater on the weekend. I love that philosophy.

I'm to the point in life where I can easily afford a car in the 50-60K range without any change to my current lifestyle but I'm also to the point in life that I've figured out that a 5-10K toy is just as much fun as one costing 5 times as much. My local track is one of those country club of motorsports and there are a lot of guys with 7-8 figure incomes driving Spec Miatas which for me tends to validate the theory that less is more.

Again I vote for play with the MR2 and then maybe considering doing things to the Forester to make it less mundane but still practical.

My 06 mustang gr8 had car seats in it forever.  We never considered selling it, plus I had an old f 150 as a winter beater.   My wife drove a c r v.  What is amazing is how fast they grow up.  My son sometimes drives the mustang and remembers hearing all the noise from the back seat. The time goes so fast, you'd be kicking yourself from selling the Toyota before you know it.

One thing that has changed for me is not having me have my kids driving older cars.  I sold our much loved  n a miata for the n b just for the extra air bag.   But again, you'll be making those choices before you know it.

In reply to Tom1200 :

I had a rental car this past week, a 2019 Camaro convertible.  It was a fun car- hearty V6, power top, good handling, etc.  But I realized that it was literally like buying two of my current daily drivers (2018 Mazda 3 Hatch).  And there was no way my mind could wrap itself around the concept of paying twice as much for whatever increment more of a car that Camaro was.  (Although I am realizing as I type this that the Camaro does indeed have literally twice the horsepower)

When I returned home and my 3 was waiting for me in the parking garage, I wasn't sad for having left the Camaro.  I was happy to be back in my 3.  

The nicest, newest Legacy GT wagon you can find?

Mine is a 98 body, 05 STI under the skin, turbo from an Indycar, '15 STI steering rack, big Wilwood brakes sized to fit inside 15" wheels with 205/70 tires.  Everything lives outside year round in the midwest.  My concession to high performance is that if it's below 0 deg I'll let mine warm up for a while before driving off (also to get some heat going).

The big difference is that mine is specifically made not to look sexy or sporty.  It's rusty, it has a big dent on the rear from a hard snowbank (almost had it!), lots of small dents from commuting (as much as possible) on Michigan gravel roads.  The paint is peeling in spots.  Casual observers and most 'enthusiasts' never give it a 2nd glance.  Only builders or racers have ever been interested in it.  But that's the way I want it.  It makes a little less than 400hp at the wheel, I get usable torque from about 2800 rpm, it's set up tail happy and the handbrake shoes have been relined with an aggressive high temp friction compound.  Which lets me have a little fun to/from work, which makes for a better day overall.

I do sometimes miss having more 'showy' cars, but I don't miss feeling the need to 'preserve' something as compared to enjoying it. 

I've thought a lot about this option. My Forester looks like it lived a life somewhere with road salt, so there is some typical rust in the rear arches that seems to be synonomous with Subarus of this era. Nothing some flares wouldn't fix. No structural rust, just a bit ugly, and sometimes have to be patient as you work on it and let the rust penetrant do it's thing. 

I'd love to hear your thoughts on your 98 as it sits, I am always impressed with the amount of grip even my stock Forester has. It's an L package, and I'm to understand that it has a rear limited slip diff, and being the 5 speed, I'm also to undersatnd it has that 50/50 bias in the center diff, but I could be wrong. Anyways, it's my first Subaru like I mentioned, and mid roundabout, if I just plant my foot, it simply turns, and continues to turn, until the body roll makes it feel like the car is going to high side. It's wild. 

Lots of broken/blown motored/crashed/whatever WRX's out this way in the PNW (STi is likely out my comfort zone on such an old chassis) that I can drag home for not a lot of coin. It's tempting as I hear everything is like Legos. 

For the folks that are asking why I don't just put the car seat in the MR2 and call it good:

A few reasons, first of which, it's a matter of household stability. Sure, it's my choice, and I'm going to stand by it, but that choice was made easier by the abundance of oblivious drivers and the fact that mountain bro's running boards on his Tundra sit at the middle of the MR2's windshield. My Wife and I talked for a while about this, and I'm comfortable scooting about it the car on a mellow Sunday, and will take the kiddo on those drives, when the sun sets at 4.30 here, and it's raining, and people still don't realize they should turn their lights on, and they just have to get to the Trader Joe's before their football game comes on so hey I've just really got to turn right now....sooooorrrry, I'm glad to have my kid in the center rear seat of the Forester. And a horn, I'm glad to have a horn. 

Second, I do lots of things. Mountain bike, snowboard, rock climb, take kiddo on runs with his gigantic B.O.B. stroller, etc., and I don't want to be reliant on one car in the household that can carry those things. Whatever is my daily driver, has to carry....stuff. Heck, even putting groceries for the family in the MR2 is a trip, but, it makes for fun conversation with bystanders.

As usual, I really appreciate the input everyone. 

The MR2 is sticking around, like I said, and the Forester is, adequate, for now. 

I do see a few suggestions for the E39 though, and I have to say, despite my earlier comments, I'm still intrigued. Shame wagons seems like they are so hard to find in decent shape, maybe I just need to go look at a sedan to get an idea of trunk space....