As a person who has owned 2 Porsches, a '98 Boxster that was bought used, and a '15 Cayman that was bought new, and is still treating me well after 10 years, and just a couple dozen miles away from the 70k mile mark, I can assure you that these cars, and the 911's of the 996 and newer generations can be fantastic cars to own and drive, or, if you're the wrong type of owner / driver, your worst nightmare.
If you're like me, a data nerd, who loves to follow processes, and can turn wrenches better than most amateurs on internet forums, then owning a 986 / 996 or newer generation car can be a very enjoyable experience, and you get to be hands on with repairing your own car. Unlike some German and Italian brands, Porsche makes their cars reasonably easy to service, in some instances.
On that '98 Boxster, I replaced the Front Engine Mount, the Rear Struts, the Water Pump, the MAF sensor, and the Convertible Top, all on my own, either in my garage or in a local mall parking lot (water pump failed while on a drive, that's where I got the car safely parked, and I repaired it over the course of a couple days), using nothing but typical hand tools.
Other quick and easy services I've done on both the Boxster and the Cayman are engine and cabin Air Filters (harder on the Cayman), spark plugs, engine oil and filter changes (no under engine body panels to remove, save 1 small one on the Cayman for easier access to 1 specific plug), brake pads and rotors, brake fluid flushes, coolant refill and bleeding (since the Boxster's water pump blew, and lost all it's coolant), and 1 microswitch for the Boxster's convertible top when that died.
The number 1 tool a modern Porsche owner should buy is the Durametric OBD connector and software.
I paid $300 for it when I first bought my Boxster back in '09, and I'm still getting free program upgrades several times a year, and it can service nearly every P-car sold over the decades.
For me, who doesn't have the income and financial reserves that some of our forum members do, I can assure you that owning a non-special edition Porsche with a manual transmission is typically a very budget friendly vehicle, if you can service the car yourself. If you are living off of a standard retail employee salary, and have an expensive rent payment, just skip the used Porsche ownership experience. Tires are expensive, and owning a Porsche with Chinese No-Name brand tires isn't a pleasant experience.
If you are the type that would rather pay a shop or dealer to service your car, the great news is that just about anyplace can service a Porsche, and no one ever complains about charging you to do so. In comparison, just try and find a place to get a modern Alfa Romeo serviced. Way different ownership experience, even though there's nothing tough or hard about serving a Giulia or a Stelvio, it's just that no one wants to deal with them in their European Car shops.
Just make sure you wallet is fat enough to pay for a shop to service your new to you Porsche, because they will charge you much more than taking your Ford Crown Victoria to your local Ford Dealer for a typical wallet flush found there.
I had to take the Boxster to a Porsche dealer to remove the broken bolts that mount the muffler to the rear of the transmission housing, and that set me back around $800, back in '09. That's literally the only service on that car that I didn't do myself. I probably could have extracted them myself, using a dremel to cut a slot in the broken bolts, and a screwdriver, but I didn't want the risk on my head at the time.
A 911 isn't going to be much more expensive for maintenance than either my Boxster or Cayman have been, but the cost of acquiring the 911, plus insurance and tire replacement costs are going to be more than both of the 2 seaters. So if you want to dip your toes into Porsche Ownership, start with them instead of a 911.
So, that's my Porsche ownership experiences over the past 16 years.
My custom ordered 2015 Cayman is my dream car, and I'm going to own it for a very long time.
