E39 replacement: E90 wagon or 550i GT or ?

So when, maybe 1 or 5 years from now, my 10 year beloved car decides to retire with honors, what should I get for a DD?
Must be a comfy, fun to drive 4-6 seater.
A quieter, more powerful and luxurious Mazda5 van would be awesome, but alas...

So. 20-50k mile MY2009-2012 328i wagon (sport package, non black in or out) or 20-50k mile MY2009-2012 550i (or maybe 300hp 535i with seating package).
$20k-$30k.
BMW-like handling.
RWD.

A new rental 320d wagon was much fun on winter tires around the Nurburgring in 2007.
A loaner 535d last winter in Houston while my 528 got aligned felt substantial and a bit porky.
I'm leaning towards a unicorn (sport, silver or blue over brown or red leather) 328. They exist.
What say you?

Any comments from those who have driven or owned either/both?
Any other suggestions? Macan in 4-5 years?


E90 pluses:
same weight as my 528 ~3500lbs
looks good, esp with sport package
red leather interior, and/or platinum bronze metallic exterior you can find one
can get manual transmission, if desired
not that big for parking, garage storage

E90 minuses:
relatively chintzy interior (not Camaro chintzy, but still)
holding value pretty well ($40k+ msrp, 70% that in 3 years/40k miles)
not that big inside, cramped rear seat

550i GT pluses:
400hp turbo V8! (445hp/480lb/ft in 2014)
bigger, better quality interior
best front seats in the world (20 way with massage, ventilation), limo-like rear seats
TOYS!
7 series platform so awesome ride quality and very roomy back seat
BIG depreciation ($70k++ MSRP, 50-60% that in 3 years/40k miles)

550i GT minuses:
HEAVY 4500+
potentially HUGE repair bills if no warranty
strange looking (but I drive a minivan so clearly not a big concern)
not substantially more cargo space than 328 wagon for a LOT more weight and exterior size.
will fill up the garage more than a 3er

 

I thought those only came in 'X' 4WD? I'm philosophically opposed to 4WD vehicles that'll never see snow or go off road, but will look into RWD 335i GTs.
They also just came out last year so second hand prices are still pretty high.
Don't think I can justify more than $30k on a daily driver so well optioned 3er GTs are still a couple years out from that.

Yeah I may have seen one 5er GT in Houston in the past 2 years.
Definitely strange looking but so much tech and power (for better or worse).

Could be tomorrow. Over the past 10 years I've steadily put money and time into the E39 to keep her on the road (eg VANOS repair, radiator, oil breather upgrade, biggest cost was replacing the rear suspension 1.5 years ago) but if anything breaks that will cost more than $1000 or so (i.e. engine or trans) then I will likely retire her.
Just in the last week the rear passenger window jumped it's tracks and the long-dormant power seat/steering wheel memory fuse-blowing issue came back.
But those are minor issues, and she drives so smooth and tight I can't bear to throw or give her away (market value $3k maybe?) until she gives me reason to.

The only new car I'm seriously considering replacing her with is a GTI. But I'd miss RWD and a BMW inline 6.

A colleague who had a 2008 550i pretty much talked me out of the 550i GT. His car needed over $10k in (warranty) repairs in the 3 years he owned it. New tranny, engine seals (multiple times), suspension, expensive tires, etc.

There aren't many E90 wagons or 535/550 GTs in the spec I want (sport pack, non black in or out) on the market. When I enter the search criteria in cars.com about a dozen of each pop up, across the entire country.

 

Interesting, hadn't read much of anything negative about the E90's durability but maybe didn't look hard enough.

I scratched the E60 off because only 4WD wagons came to the US.
A 535iT with RWD like the ROW got would be a definitely contender.

You are correct about the E39's greatness. It's the complete package and even now almost 20 years after it's design nothing I've driven can top it as a do-it-all (except moving large furniture or carrying more than 5 people) car.

lol hard to let go of a good E39 isn't it Jeff
And even harder to replace evidently...

Now you two have me considering (for roughly the 150th time) replacing my 150k mile E39 sedan with a clean E39 wagon.

This one has the same (great) color and BBS 2-piece wheels as mine, but it's not a true "Sport" since the base steering wheel and chrome window trim:
2001 BMW 525 i, $9,850 - Cars.com

However, way I'm getting a manual transmission in Houston.

Here's a 540 in a fantastic color and with still reasonable miles, WITH the coveted Sport pack and auto trans but black interior would be hellish in the summer and dark and dreary all the time:
2002 BMW 540 iT, $12,995 - Cars.com

Sometime I wish I saw daily driver cars as mere appliances like most people. Or that I never bought an E39 so choosing it's replacement wouldn't be so tough.