groovzilla

Dealerships usually get trade in's or Auction Cars which can be hammered from lack of care/etc. I've seen terrible nasty examples of Porsche's at dealerships left outside in the weather. There are some nice examples but they are way overpriced.
My 107K 997 C4 is purchased from private seller - tight and clean and drives like a 50K car and trust me I've had enough 997's to compare. Lots of Porsche owners take excellent care of their cars but some not.
My car had only 3 owners, always garaged and last 7 year owner I purchased from was Boeing Engineer who babied it. These cars are out there however it can take patience for the right car to be found.
I really suggest finding a private party car if possible. I've only bought 1 Porsche (996) years ago from a dealer and I regretted it. Paid too much.

As far as Automatic, I can understand the body pain. When I got into my 50's I noticed my sports injuries making it difficult to even get down into the seat of a Porsche. At 63(64 next month), I get in head first and use my knees on the seat and hand on center console to swing around down into the seat. But I can't drive anything but 6 Speed Manual and I don't have any pain shifting. For me it's the reason I own a sports car. Shifting all part of the fun.

TT------> I like the 997 TT body headlights much better but I know the 997TT is higher priced than the 996TT. I also never liked the TT body style. Even during my early 911 days I never liked the 1970's - 1990's Turbo's. Just not my taste but that's all personal preference. I've never owned a Turbo.
I think you can very easily find a nice well serviced non-Turbo Automatic 997 to fit the bill.
Personally I prefer higher mileage 997's. #1 if you PPI/Bore Scope Inspect and all is great, the odds of Bore Scoring at say 80K or 90K miles is much less and the non-S motor much less prone to scoring.
My way of buying a Porsche & Mercedes for 35 years is to buy a higher mileage car that is well taken care of/babied by responsible owners with service records and have had the major services done, Brakes/Thermostat/water pump/belts/pulleys/coils/plugs/etc services completed so there isn't a laundry list of items needing attention for a long time.

If it were me, I'd try and find a 80K-90K 997.1 that has excl service history and clean PPI/Bore scope Insp. Finding a car that has always been garaged is a plus. Such a difference in body trim/molding/paint condition. I've noticed this with cars in California that have sat out in the sun for years. Garaged cars much much nicer.
Can't go wrong. should be able to find one in the low $40K range, some even in the $38-$39K range.
They are out there and will be coming on market. Economy is tanking and I see many more 997's for sale now. Check out the PCA Classifieds website - They have lots of cars coming for sale. Just had a 2007 997 w/3 PCA member owned all service records for $38K but just sold.

Keep us posted with any questions on the 997's you have interest in.

Enjoy the hunt.

RubyRose

Wow! Cant's thank you enough for engaging with me on this hunt. Great pictures...looks like you really have experienced the ins and outs of 911 ownership.
Just found a 2002 996TT tip. 2owners. 60K miles. fixable headlights( turns right under headlight...) Checking on any services records.???
Also been looking at an 06 cs tip with 47K miles Asking low $40's Great color combo with sport exhaust.???

groovzilla

Sport Exhaust a great option! a couple of my 996's had Sport Exhaust and a few of my 997's. My current 997 has Fister Mufflers which is very close to the Sport Exhaust sound.
I forgot to mention another good reason to buy from private seller is ability to grind seller down. Got to learn the art of the grind.
I should write a book on it. Negotiate a purchase price then get the PPI/Bore Scope Inspection. After you get results come back to seller with any items needing attention and start grinding again.
Be firm & polite.
Keep us posted!

BTW I was heavy into the 356 world 30 years ago. Loved them and owned lots. My favorite is my 1959 Super Sunroof. I restored it 22 years ago.
Here are some photos of my earlier cars - 1959 my birth year was particularly special to me - I had many '59 356's

sandwedge

Maybe I missed it but I don't have a clear picture of your budget. I have an idea but not if there's any flexibility. Reason I bring this up is that if you could stretch your budget a little bit you don't seem too far from a higher mile base -09 997 with a PDK. I've driven manual 997's, TIP 997's and PDK 997's. Since you don't want a manual, try as best you can to get into a PDK rather than a TIP. Difference is night and day since the TIP is a regular automatic...torque converter and all as opposed to the PDK which is a manual transmission with two clutches but no third pedal. If you haven't read up on it you probably should.

Another reason to try to get into a 2009 PDK is that you also get a much improved engine. The IMS bearing is gone and supposedly, the cylinder walls have been redesigned/strengthened, reducing the risk of bore scoring.

One in the + column for the TIP is that it seems just about bullet proof. It was ordered on a lot a of turbo cars since along with its robust reputation, it actually beat a manual turbo on a 0-60 run. So will a PDK but the PDK doesn't have the same almost fail proof reputation as the TIP. Lots of stories on this if a 2009 or later with a PDK becomes a consideration. Good luck whichever path you decide to take.

Doug H

Don’t get a tip unless you get a turbo. I had 3 996tt and they a great card. I had a few 997s including a GTS. Great cars in either pdk or manual.

if set on tiptoeing, the 996tt hands down. Maintenance can be a little high on the Mezgers.