I agree with everything AKnowles said - an excellent post and excellent advice!

Brad

Lots of great advice here for you. There are true sports cars and then there are sporty cars. The 986 is a true sports car, you won't regret driving one. With an 18K budget, you can get a great S model for less than $15k. Take your savings and get the IMS taken care of, if it hasn't already, and then drive it like you stole it:D There is no comparison to the 350z IMHO. I drove a few 350's in my search and it is a nice car, but it is not a Boxster.

I agree. Personally a 3.2 with an updated IMS it the best value proposition.
You get the upgraded cylinders (not found on even the 3.4 Carrera) to eliminate D-chunk engine failure (a problem with low mileage 2.5 and 3.4's). And relative to later 3.2's the weight is lower. Again, Personally 250 HP with a little room for more with some upgrades, weight dropping (18-20 lb. wheels, GT3 seats, Optima battery) to get you to maybe ~270 HP, on top shelf rubber, and you've got a car that's quicker, better handling than nearly all of the pre-2000 NAflat6 Porsches. Ditto for some old Ferraris. And unlike a 993/964/911, that owners are too timid to drive hard for fear of wrecking/depreciating, these cars you can drive hard, in any kind of weather.

I was in much the same position as you....
 

I was around ~27 years old and looking to purchase my first home. I bought a '00 2.7 with 33k miles about a year before I bought the house and wondered what the maintenance costs would be like. I had two 300zx's (1st and 2nd gen....really miss the 2nd gen) before the boxster but had always wanted a boxster since I had first witnessed the concept car as a teen in the early 90's. I purchased the car in 2007 I think and have now had it 6 years or so and for the most part it has been a fairly reliable vehicle and has never left me stranded. The car now has 85k miles and for the first 4+ years of ownership it was my only vehicle and a daily driver. I now drive a nissan hardbody truck as a DD and drive the car once or twice a week and put about 5k miles a year on it. Over the years I have had to replace the AOS, window regulator, two sets of tires, muffler (just for aesthetics), air flow meter, convertible top, brake pads and rotors, and the waterpump/hoses. I do everything myself as the closest specialist is about an hour and a half away. Having a second vehicle is a really nice fall back plan so I can take my time doing whatever I need to do to the car. You can find a lot of good cars well under your max price you listed and I would probably go that route and put the saved money in the bank for repairs if needed down the road. I would not discount the 350z as my best friend had one and it was a great car and very reliable...the convertible version looks like crap IMO but they are a lot of car for the money, especially if you can find a track model. Whenever I am financially able, I plan to get another 300zx to park next to the boxster someday as they are great cars.

Thanks for all your advices guys,

I'm seriously tempted, I will think about all that before taking my decision, but buying a little lower than my budget makes sense.