I’ve been a Porsche nut for years, love almost everything they’ve made as long as the word Panamera isn’t on the back. I’ve watched oil cooled 911’s evaporate out of my price range. I’ve come close to buying a 944 in the past, but it’s never panned out.
I’m probably looking at buying a new car next year, the original plan was to buy a new Mustang, but even with my A plan pricing, whenever I price out a Mustang I want it keeps coming out the wrong side of $40K, I just don’t want to spend that much money on a car. So for a while now my intention has been to buy the a 986 or 986 S for cash in the $10ish K range. Then immediately do the IMS bearing at clutch where ever I had the PPI done. Bonus points for it coming from Southern Cali as an excuse to fly out and drive it back across country with the spousal unit. I’ve always loved driving Boxsters. The intimate go kart like handling with wonderful steering, still coupled with a ride that works on Michigan’s special stages, err sorry super smooth streets. But my wife has never been that enthused, she finds the lack of torque annoying in the two base cars she’s driven. We’ve both driven and like 944’s in the past, although it’s a long time since she’s driven one and I’ve never driven a 944 and 986 within any sort of a time frame that makes a back to back comparison possible.
So my brain has begun ruminating on a 944S2 cab as a good weather DD keeping the Volvo for inclement weather and the chilly seasons. 944’s will be a lot older than a 986 and have more age related issues. But they don’t have the potential high $$ down falls that an M96 can have. As long as you keep up on the timing belt and with the 16V engine the chain tensioner they are reliable as gravity. Yes the clutch is a two weekend job without a hoist, but it can be planned for. A 944 is also probably past the low point in its depreciation, so while I’m not a car flipper and keep my cars a long time I would at least be assured that my money it wasn’t’ loosing value. There is also the 951, but there are fewer cabs out there with 951s. There is also the 968, but it just doesn’t have the purity of the 944 in its lines, not that I’d discount it. Part of this was kicked off by seeing this 968 cab on Sunday morning in Ferndale, it was a tiptronic though which is a complete non-negotiable no no.
BTW, why a cab? I like convertibles, the spousal unit loves convertibles. I know they down't work for track use as well but that's OK. I can kid myself all I like that I’m an autocross and track day guy, but the last autocross I remember doing was about three years ago. The last time I was on a race track was 2008 when I picked up the Volvo in Sweden and drove to the Nurburgring. Evidence says I’m not a track junky anymore. I do theoretically have the Saab for autocross and track days, but the reality is I’d probably sell it to help fund the Porsche.
So, Porsche gurus, talk to me of 944s and 986’s. DD ability, comparison in ride and handling, long term ownership etc. Entertain me and convince me one or the other is the answer and that I should go and buy and NC PRHT Miata and throw a Targa package at it from FM instead.
The 944 is better built interior wise and has more storage capability (even in cab form). Engine is a bit uninspiring IMO, but is torquey and can move it along nicely. Chassis isn't the best, but they've made a lot of improvements over the years and the aftermarket is still going strong. Most of the issues have been worked out and 300K isn't unheard of on well cared for examples.
The 986 was built with seemingly less care due o the price point so they can be more noisy inside and tend to have random stuff break a bit more with lower quality materials. The 2nd gen is much better apparently. Mid-engine and suspension are ultimately better for high performance stuff. Storage space isnt quite as good. Engine issues are a concern and maintenance can be more difficult.
That said, I'd go with the NC PHRT and just drive it. The P cars wont be anymore fun or fast on the public roads and their maintenance will be more expensive in the long run. Unless you're planning on waiting for the collectible market to come around, it isn't worth it, IMO. There's a reason I sold my 951S and I'm shopping for Meotters, the fun to $ ratio is just much better IMO.
Both 944s and 986s are great cars.
944s have awesome 80s styling, if you like that; I do. Hatchback design is convenient. Great weight distribution but has more body roll and dive and squat. 944 seats are better than 986 seats. Interior has aged well and is functional. 944 sunroofs are inferior, I think, because they only tilt or lift out; they don't slide like most sunroofs. I've only driven the 2.5 liter 8-valve engine, and I find them lackluster.
986 has, between the trunk and the frunk, a lot more storage space than most realize. However, interior storage is lacking. 986 clutch take-up is rather poor; many experienced clutch drivers struggle for smooth launches in normal driving, and even once underway shifting can be lurchy. Engine is great fun, even the early 2.5 liter. Induction howl over 4000 RPM is awesome. Convertible top is good. I get tired of turning traction control off all the time. 
986 offers amazing performance when driven hard: it's fast enough to be fun but not so fast that every drive is a ticketable offense. It is hands-down the best chassis I've ever autocrossed. For hard driving it will slaughter a 944. Every time I drive a 986 I like them better and better (and I started as a skeptic).
Both cars will require maintenance spending, for different reasons. The needs of both cars are well documented. If you buy a 944 Cabriolet and a 2.5 liter Boxster and pay to cover all the required maintenance and IMS issues, I'm guessing the Boxster will cost more but not a lot more; I think the Boxster's likely lower miles and higher performace will be compelling compared to the 944.
This is an interesting comparison. Let us know what you find and decide.
In reply to DWNSHFT:Phew, I was getting depressed after Turboswede's post, what happened to all the enablers on here? I was expecting someone to tell me to man up and buy an early 00's Maserati instead GT/Coupe/Spider for the same price instead 
(yes, they are out there sub $15K, yes I thought about it for at least 30 mins before my brain tried self Aneurised (yeah, I just verbified aneurysm) to protect me)
Anyway back to Stuttgart's underappreciated finest. I'm not too worried about 944 sunroof's as I'm more inclined towards cabriolets as once I've given up the idea of tracking, a soft top is better than a hard top 12 times out of 9, except possibly in the looks department. Anyone have any experience with 944 cab top mechanisms and tops, are they durable and easily fixable like an NA Miata, what is NVH Like when they are up? I've been in 986's with the top up and down, but never a drop top 944?
It's funny, every generation of Porsche engine seems to have its Achilles heel, but once fixed (thermal reactors, pop off valves, head studs, timing belts, IMS bearings etc.) they all seem destined to last 300+K with routine maintenance no meter the number of cyls, layout or cooling method.
I'd rate Porsche as probably my favorite car. I truly miss my 951 and place it easily in the top 10 of every car I've driven. It's not the best at anything, but as an overall package, it's almost perfect. But I really, really want a Cayman or a Boxster. There's something about them that makes every drive a special occasion.
I know this adds nothing to the conversation, but I vote get a Porsche and don't worry about the problems. After I sorted my 951 and caught up on differed maintenance, it was pretty reliable. Same is true for my NA 944.
In reply to Adrian_Thompson:
I'd like to help, but I haven't been able to choose between a 944S2 and a Boxster S. That's why we have had both for the last 11 years.
The Boxster S is slightly quicker and feels more agile and athletic, as one would expect of a newer, mid-engined car. The 944 has more of a vintage look and feel. The 944 allows for more leg room, so, for a tall driver, it is more comfortable on long drives. And it has those little back seats, which are good for kids and can even be used by compliant grown-ups for a short ride. The flat six in the Boxster makes nice Porsche sounds.
As always with Porsches, it is worth paying more for a good example because it can cost so much to fix one up.
In reply to Danny Shields:
Interesting that you say the 944 has more leg room as a DD.
In your experience, times, classing and competitive ability aside, which is more fun / rewarding to hustle either through the cones or down your favorite twisting road?
What is your running costs and maintenance experience with them?
Cheers
Adrian_Thompson wrote:
In your experience, times, classing and competitive ability aside, which is more fun / rewarding to hustle either through the cones or down your favorite twisting road?
For fun/rewarding during hard driving, whether street, autocross or on track, 986 > 944. Mid-engine balance is awesome. The dive/squat of the 944 is an additional detractor. 986 motor is waaay more fun than 944. Boxster/Cayman is one of my mostest favorite performance chassis, based entirely on subjective feel/fun, not lap times. [Other favorites are E36 M3 and Lotus Elise.]
David
Adrian_Thompson wrote:
In reply to Danny Shields:
Interesting that you say the 944 has more leg room as a DD.
In your experience, times, classing and competitive ability aside, which is more fun / rewarding to hustle either through the cones or down your favorite twisting road?
What is your running costs and maintenance experience with them?
Cheers
In the Boxster S, I move the seat all the way back and down, as far as it will go. And I still wish it went farther. When I drive the 944, I don't even use all the available seat travel.
Since we got the Boxster S, it has been the autocross car and the 944 only runs one or two events a year. I guess that tells you something.
When we bought the Boxster S it was two years old and by far the most expensive car we had ever bought. We didn't know how long we would keep it. But after all these years we still love driving it and plan to keep it forever.
They have both been pretty durable, but I keep up with the recommended maintenance, not just oil changes but belts, brake fluid, gear oil, etc. The S2 had 96K miles when I got it 15 years ago and has 203K now, but still looks nice and runs great. Porsche builds cars for long life spans but you have to take care of them.
I've owned two 951's, one stock and my current LSx swapped one. I'd get the Boxster S in a heartbeat for your intended use.
It's a much more modern package and an extremely well balanced car. Get one with the glass rear window...
986s are understated, but always bring enjoyment and a smile when taking a drive. Vastly underrated
I've owned both. I would go 944 again.
944 always fit me well, it's a momentum car that is a great car for dailying and weekend jaunts. People really respond well to it, non car people recognize it and are inquisitive. Upkeep on the S2 never felt as bad as it did on my older 944s, this could be because I bought a nice convertible and the hardtops were mostly piles. I think I paid 9500 and sold it for 12500 on eBay.
Boxster is a good car, powerful enough as a driver. I had an 01 S with tip so my experience will be atypical for this forum. It needed nothing beyond scheduled maintenance(and a couple splices, see below). Interior is not super nice in the way a car that cost that sort of money is expected to, I seem to remember the wiring in my doors breaking at 40,000 miles which was a bit frustrating. Windows and speakers went out. Non car people turn their noses up at you for some reason. I think it was $36k(2004) and sold it for $34k (2006).
At this point finding "good" specimens in your price range may be hard, 944 converts aren't exactly on every corner; most are 1 of 40 or so because of the limited production and odd optioning. 986 are bottom of the barrel cars and were treated that way by their owners in a lot of cases. I think you'll be happy either way, good luck!
Certainly enjoy my cab - just hit my 5-year anniversary with it. You certainly don't see yourself coming or going, and I for one love the torque from the 3.0 L. Handles like it's on rails, great for carving up mountain roads here in NC. Two things with these in addition to the normal 944 items such as timing belt - first, the twin cam cars have plastic cam chain tensioner pads that become brittle with age and can crumble, causing catastrophic damage to the head. Change these immediately if you purchase, easy job and well worth the peace of mind. Second is to convert the top to manual mode - if the motors ever get out of alignment it can break the main bow, which is apparently made of Unobtanium. Again, easy fix to disengage the power top. All in all, mine has been relatively inexpensive to own and pretty much trouble free-purchased with 86k and now have 115k. Regularly makes trips to VIR and Road Atlanta, great road car.
Ade, this is a purely personal decision, and you know it. By any objective measure, the Boxster is a better car. It's faster, it handles better, it's mid-engine, it's more modern, it's more reliable, hell it probably gets better mileage, to boot. But it's not really "special", at least not in mid-2015. Now, granted, an old 944 isn't all that special, either, but at least you have the nostalgia factor going for you, and that's big for Gen-X-ers like us. And the styling. Again, this is personal, but to me the 944 has aged a lot better than the "smaller 996" look of the first-gen Boxster. Maybe in another 20 years we'll look back more fondly on the 986, but for now it's a pretty generic late 90s shape.
In summary, the 986 is better, but the 944 is cooler.
