My '99 XK8 convertible is my dream car, after 40 years of Jags, BMWs, Mercedes, etc. The key to happy motoring with these cars is 1) inform yourself about the issues, mainly the 4.0 liter's needs re upgraded timing chains, tensioners & water pump, and 2) have a local Jaguar specialist (not dealer) who can bring them up to standard & maintain them there. My XK8 cost me $5800 in 2015 with perfect body & interior, no accidents and with the engine upgrades already done & convertible top hydraulic lines replaced. After new tires, shocks, motor mounts, front brakes, mass airflow meter, valve cover gaskets, plugs & filters, she now runs & drives like new for a total all-in price of around $11k. I couldn't be happier.
UPDATE: 15 months into ownership of my '99, I've spent very little on the car except for oil & gas. Classic/specialty auto insurance (Hagerty) has reduced the cost of comprehensive insurance to less than $400 annually on an agreed value of $15k. Costs since the initial review have been limited to a new Jaguar ignition coil ($128) & professionally repainting the front & rear bumpers (approx. $600), a project I intended since purchase. There have been no other costs; everything works great on the car & it runs & drives beautifully.
I still marvel at how much car you get with the XK8, compared with much more expensive GTs like an Aston Martin DB7 or (especially now) Porsche 911. It took nearly 20 years for the XK8's predecessor, the XJS, to begin to appreciate in value, so it will be awhile before XK8 values start climbing. In the meantime, buy the best accident-free XK8 you can afford, have a local Jaguar specialist maintain/service it, and take care of it like it deserves. Great value, great motoring, great experience.
UPDATE (5/16/17): 30 months in & still loving my XK8 - she's a keeper. A few months ago, I decided to fix some miscellaneous leaks (oil, coolant), a part of owning any British car. My local Jag specialist replaced the coolant bypass hose, water distribution pipe & thermostat housing, plus some o-rings & the coolant cap. The shop also replaced the oil pan gasket & drain plug. The fixes weren't cheap but they worked. Costs: parts ($321.32) & labor ($284.20) totaled $624.80 w. tax.
The car is now approaching 130k mi. & drives as sweet as ever. I'm planning some road trips for the summer, including a couple of British car shows. The body & paint is excellent, the black leather interior has that aromatic richness of Connolly leather that I love, and the power top, AC & electricals all work perfectly. It's still a few more years before XK8s start their upswing in value as a modern classic, so find a good 'un now while they're cheap & enjoy!
UPDATE (5/17/18): Quick update on my XK8 after 3+ years of ownership - she still looks great, comes out of the garage on sunny days, and runs like a top. No issues at all during the last year - I've added about 2000 miles since the last update. Hard to believe my XK8 is approaching 20 years old, but it's true. I sometimes get a yen to sell it & get something else, but what would take its place? A drive in the country, top up or down, is all it takes to remind me what a great car it really is. She's a keeper.
As someone who has owned two other Jaguars, an XJ6 and an XJ8, that were purchased new and kept for 7 or more years and 100k miles, without any problems, I was optimistic that my purchase of a 1999 XK8 in the spring of 2010 would not present any problems. I researched the car and was aware of the timing chain issue (which I replaced immediately on purchase of the car), but I was unprepared for mysterious "check engine" light problems. After several unsuccessful attempts by my repair shop the problem ultimately was the electronic throttle control module (a very expensive part). After replacing the ECM - no problems. All in all still a lot of car for the money!
Smooth ride, good all around performance, great lines and quality.
Bought this gem used with 21K miles on it. Good thing I had an extended warranty. Plenty of electrical problem, traction control fail, antilock brake fail, convertible top lines fractured (not covered), fuel pump fail, starter fail, etc. In spite of all that, this car is just fab. It drives like a dream now that everything is fixed. She is a thing of beauty. I never get tired of starting the engine. She handles so well on the road and is great on the highway (gets 26 mpg believe it or not). These cars have lots of computer glitches. You have to get used to them. Thing you need most is a mechanic you trust who can keep your gem running smoothly. Dealerships are not always the best at this.
I love the convertible top. That's the whole reason you would buy this car. You need to drive with the top down AND the boot cover ON. This keeps everything clean. It is not a big deal to put it on. Yeah, it's not as slick as other models, but that was the way it was in 1999. HK stereo is awesome.
It is a classic car. It is what it is. Buy one because you love it. I plan to keep this one forever. People offer me money for it all the time. Plastic parts do wear out after 10 years so be prepared to replace them (cup holder and sun visor makeup mirror).
I just bought my Jag Xk8 convertible a few months ago. It is black on black with chrome wheels. The car gets plenty of looks. People cannot tell what year or what I paid for this baby. The car is beautiful to look at in motion or while sitting still. Under the hood is a monster. the car has power the run a quarter mile when needed. In short, just buy it. You treat the car good, and she'll treat you real nice.
Timeless look, comfortable ride, and great handling.