So my first first Porsche experience was back in 2009 and didn't go so well. Back then I wanted a newer model 911 so I started my research and became aware of the possible engine issues. I decided on a 996 turbo because the engines, at least according to my research were much less prone to failure, bulletproof, etc, etc. I finally found my car, a 2004 turbo cab X50, fully loaded (window sticker 155k). I ordered a ppi because the car wasn't local and all good. Approximately a year and 1700 miles later an ominous clunking sound develops. Long story short, 16k dealer repair and the Porsche love affair was over, the car was sold and I soon became the owner of a brand new 2006 Corvette complete with new car warranty! The Corvette didn't last long and has since been replaced many times over. Fast forward to a couple of weeks ago and I get the Porsche itch again.
This time I decided on a Cayman S and the chase began. I had a few potentials listed but just for comparison I tried a craigslist search. One car caught my eye because firstly in was a preferred color (cobalt blue with color matched factory rims) and secondly the price.....18k for a Cayman S...! The car was an '07 with high mileage (for a Porsche) at 104,000. The ad consisted of a few pictures and a brief description that mentioned excellent condition. The VIN was listed so I ran an autocheck that scored 92, I also searched and found the original build sheet through the VIN and an original sticker price of $70,640. I arranged a viewing for the very next day. The seller and second owner had bought the car from a dealer CPO with 40,000 miles back in 2011. The car had a full service history up until he bought it. Since then (other than a clutch 10k miles ago) he had done all his own service work, he had even filled in the service book! Yeah, yeah, sure. I've bought a bunch of cars over the years and I'm not the gullible type!! 😬 I was dubious but this seller ticked all the right boxes, he worked as an engineer, owned another Porsche, had a spotless garage etc. Anyway, the car was in fact in excellent condition, was 100% original (other than a Pioneer head unit with Bluetooth) even the factory wheels had zero curb rash so I bought it on the spot for a bargain price of $17,000 (less than half my original budget). The car feels tight and handles superbly, ive had the car for 6 days and I'm one happy owner.
In summary, my first Porsche was a fair weather, weekend only, pampered, top of the line 911 turbo that turned out to be a basket case. My second Porsche a well driven, daily driver, 11 year old Cayman S, will it be a better experience this time? .........Only time will tell. Opinions on and model specific advise/suggestions appreciated.

"I used to be indecisive but now I'm not so sure"

Just reread my post and noticed my dates/years are off, I bought my first Porsche in 2006 and the car was an '02 turbo, not an '04.........whoops!

Interesting and coincidental, I had a 99, 2000 Andy then 2002 996, I had the IMS done in addition to Clitch etc. at about 75K I suffered catastrophic engine failiure (I believe it was a Schorched cylinder wall) In my haste and anger at the car line, I went out and bought a new Mustang GT convertible. The novelty lasted all of 6 months a and now I have a 2011 997.2. .. love it but let’s hope this PDK is as flawless as claimed :-)