Strategy, choices
 

I have a great 1987 Carrera. It is in excellent condition and runs like a top. However, these cars have significant limitations(AC, overall speed, etc.)
I have done one DE day in the 87 and it was fantastic. I was amazed at what these old cars can do.
I'm not the guy with the finances/skills to act like a collector, so I would not want to spend more than the two options below would require.
I am interested in a more modern car. I had driven a 2008 Cayman S once back in 2014 but didn't drive it hard. I drove one last week and was amazed at how it drove-I loved it.
I know there are IMS/oil starvation issues with 2006-2008 Caymans.
So here's the question.
Would I be better off keeping the 87 and buying a 2006-2008 Cayman S, or would I be better off for about the same money of what I could get out of the 87+ cost of Cayman S, buying a 2012 Cayman R or 2014 Cayman S?
Pros and cons from what I know
Keeping 87 and buying older Cayman S
-pretty much all depreciation gone
-2 types of cars/experiences
-probably cheaper insurance
Cons
2 cars to maintain
2 cars to insure
potential normal issues with having 2 cars that are off warranty
Not sure I'm all that comfortable driving a 50k plus car-I initially got into this as a hobby....

Keep the 87. You will regret selling it.

What's your age?

Do you have garage space for an extra car?

I've had air cooled 911's and a Boxster. I loved them both. The handling of the Boxster was unbelievable as was the air conditioning. The old cars are a hipper conversation piece but the newer cars are a lot easier to drive, have a job in, much more lady friendly, and safer because of airbags/crash protection.

If you're relatively young keep the car, assuming you don't have to pay to store it. If you're paying for storage any future profit will be eaten up by storage fees. Pickle the car, put it up on blocks, return it to stock in anticipation for later sale.

To me it makes no sense to have multiple cars that serve the same function.

If you still want a Cayman, get the 2009 model year. Starting to become affordable. And keep the 87!

The Cayman is an incredible driving machine, better than the 3.2 in every possible way.

However, the 3.2 smells better, the doors shut better, the engine sounds better, the wheel feels better in your hands, and, selling it would bother you the second it leaves your driveway. A group of special men built that car by hand... they are mostly gone now and so is that era.

Choose wisely, you most likely will get priced out of the 3.2 quickly.

Thanks for the thoughts everyone!

Totally this! They don't make them like that anymore. And sometimes less is more. It took us a long time to figure that out.

Keep both!
I sold a 2006 Cayman S that we bought new to buy a 89 Carrera. (This was 3.5 yrs ago, so I had $ left over). We owned a '82 SC for about 15 yrs prior to buying the Cayman. I missed the sound and feel of the old 911. (My wife says the '89 rides hard, is noisy, is hot, and stinks, But.. I like that.

I figure it this way.
You can't rationalize owning a Porsche. If you try to (and I have) you'll sell it and miss it the second you see it leaving your driveway. I do miss the Cayman S. But it's like missing a fine tool that was misplaced, you know you can buy another. Old 911's are much harder to find in today's market.

RE: If increasing values make you worried about driving a old 911, let me tell you how I think about it.
If one buys a new semi luxury car or fancy pickup, you'd be in the ball park of a really nice old 911, and you wouldn't think twice about driving the new car. Reality is the new car is loosing value while the old 911 is going up in value. So, drive it and enjoy the increase in value.

Good points triplnet. Thanks

I agree with the sentiment (keep the old car) but it's not really comparable to a new car or pickup, just because the new one is depreciating and the old 911 isn't.

If you wrote off the new car in a collision you can easily replace it. Not so much with the 911. At the very least you will likely have a hassle with your insurer over the increased value.

This isn't stopping me from driving my '85 though! ;)

Cheers

d.

The IMS thing is way overblown. If you aren't running the Cayman on slicks on track you also probably aren't generating enough Gs to worry about other oiling issues either.

I recently bought a 986 Boxster from a Pelican. Like yourself, I wasn't really sure I wanted to track my IB cars anymore even though they are a lot of fun and way faster than many more modern cars.

Keep the Carrera. Buy the Gen 1 Cayman. Track it. And still take the Carrera to the track once a year or so. There's nothing like driving the old cars at their limit and you can't do that on city streets without being a menace. Also probably more likely to destroy your car on city streets driving that hard than on the track. ;)

There will always be a faster car than the one you own...

There will always be a more expensive car...

There will alays be a car that handles better...

Keep your 87, and just drive it. Become the best driver on the track that you can be, in that car. You will learn more about driving that 87, than any cayman could teach you...

Whats the old saying, "Life is a journey, not a destination."

If you want the cayman because its faster and handles better than the 87... be aware that some guy in a vette who spent half what you did will probably blow right by you...

If you want it because you always wanted a cayman, then go for it...

I know a guy...
Doesn't everyone?
PCar DE. Great guy.
Cayman S with over 200 track days and hit almost a 100k miles before the engine went belly up. I find that just incredible. That's a ton of hurt and mileage before needing an engine?