hmm...coming from an E46 M3...first thing you'd wanna swap out would be the damn skinny Porsche steering wheel...

go with the TT you will have so much run riding it.

I'd get the SL55

Turbo will hold the resale value.
997 and SL will kills you if you wants to sell it in the future.

What are the maintance costs like on a 03 996TT w/ 25-30k miles? If something major breaks and the car is out of the warranty, will I be stuck with a $10,000 bill? This is my biggest concern, at 70,000$ I'm already stretching my budget and really don't want to deal with potentially costly repairs... same thing with an SL55.

I'd say get the 996TT. I drive mine everyday unless there is REALLY bad weather. Get the EasyCare aftermarket warranty. It's like $2000-$3000 depending on if you want a deductible. I have one on the 02 and it's covered for 3yrs or till 60k miles. The car had 14k when it arrived.

Both 911s are great cars and fun to drive. If it were my only car and daily driver, I'd go for th 997S because of the warranty. After driving the 997S and the 996TT, I chose the TT but I have a daily driver. From everything I've read, if the car hasn't been abused they are rock solid. So you could go for an '01 TT ($55K) and get a BMW with the difference. The biggest problem will be which to take to work in the morning.
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2000 540iA Sport (DD)
2003 996TT days away....

get an RS6...problem solved...

I think all are good choices and personally I love the TT and think all three would be equally reliable. Dropping the mercedes out I like the TT due to the fact it has the GT1 engine block and dry sump which is a superior engine.
All that said from what I have read here your best bet is probably the 997.

you could always go with a brand new RS4???? Fast as hell and under warranty...

You should be able to find an '04 SL55 still under MB warranty at your price.
The normal maintainance is covered by MB until 4 yrs, 50k.

A great after market warranty (0 deductible) is $2,100.

The SL rides better than the TT but you will be more involved with the TT drive. You will drive more aggressively in the TT. The driving dynamics are really different between the cars.

If the top down and softer ride are important - get the SL.

Ya Martin.....we both have G35's and GT2's.....I think I deserve some rep points, lol.

To the OP, I would want an income of over 100K before I would DD a TT. The TT is very reliable for its performance level, but you will still be paying a bit more than one dollar per mile when all is said and done. I would also have a house w/ equity and good progress saving for my retirement. If all those things are in order then I would go w/ a high end car.

It wasn't until recently (after I turned 40) that I could responsibly afford my current cars. Previously I drove Toyotas and Mustangs.

Where do you live? I lean towards the Turbo...

here's one (mine...haha)..

http://cgi.ebay.com/ebaymotors/Porsc...spagenameZWDVW

look at this one in the classified, im sure u can work him down to 70k
https://www.6speedonline.com/forums/...ad.php?t=67576

no matter how 'bulletproof' a car may be, a 5-6 years old car is still a 5-6 years old car. all the joints, seals, hoses etc etc will be 5-6 years old.

I went from a very well taken cared of, relatively 'new' e46 m3 to a few years older, what appears to be an immaculate version of a 996tt because I couldn't find/afford a GT3 at the time. All I can say is, while the car is 'bulletproof' (so far), the car will never be as 'perfect' as a newer 997. I'm not saying I would take a 997S over a 996TT, but I think while the phrase 'bulletproof' is tossed around alot on this board, I feel like potential buyers should be more informed. With that said, you can't go wrong w/ either, but i'd drive both more than a spin around the block. best wishes.