In my youth, I drove Alfa Roadsters and a Porsche 914. Then I settled down, bought a BMW 2002, got married and had children.
After the house was paid for, the college bills paid, and the retirement secure, then, and only then, did I buy a Boxster.
Looking, I drove every roadster imaginable. Corvette, Jag, Honda, BMW, other P-cars etc.
My impression of the Honda was that I felt confined in the cockpit (I was 6" 230 at the time) and didn't like the buzz of the engine. It also lacked trunk space for the trip to the beach/mountains with my wife I had envisioned.
I wasn't pro-Porsche as my 914 experience was not good in the quality of car or dealer service areas.
My first drive in a Boxster had me inside of 10 minutes. I drove it to an interstate, up to the next exit, dropped the top, drove back and began negotiating hard. Lots of room in the cockpit, luggage space fore and aft, and would pull from 1k easily. Quiet cruiser. Enough car so that it was better than I was a driver.
I bought a '99 base Boxster. 2.5 and 4 months later totaled it through inattention ...actually I was busy admiring another Boxster in a parking lot by the side of the road. When I got the insurance settlement, I immediately set out to replace the car (and since the settlement was more than I had paid for the car and it was a model year later, I decided to sample the S model). I found an '01 S, got a Pre-Purchase Inspection and bought it. I could have had the 3 years more extended warranty and paid $3k or the seller could turn in her warranty, get a refund and charge me $3k less. I'm one of those people who self insures because I don't like the odds of doing better on an insurance policy when its cost has to cover so many selling and administrative expenses (and payout from such policies averages ~20%). I declined the warranty. Now 4+ years later, I came out way ahead. In unscheduled maintenance, my costs have been less than $15 a month on average and the car has never left me stranded. (I had no repairs at all on my first Boxster in 4 months of use as a daily driver.) My second isn't a daily driver any more simply because on the average day I don't drive a car. But my wife doesn't have to ask me twice to go to the store and she knows I'll take the longest way possible. I even take the trash to the dump in it (and I have a CRV I could do it in but...). I love the car.
Both my cars were 2 owner cars when I bought them. Both I knew the maintenance history from paper records the owners had.
I buy the best tires and battery and such for the car. Have 15k on the rear tires and can see another 3-4k before I have to replace them but, when I do, that will be ~$550 for the rears alone. I could buy cheaper tires but I want the best between me and the road and I can afford them. I do perhaps 1/2 of the maintenance on the car, 1/3 at some random mechanic's place that has a lift and the dealer sees the car every 2-3 years.
I could have bought newer cars, never felt the need to. I can have 98.3% of the fun for well less than 1/2 the price buying used.
Porsche people are fun people and I've been to local get togethers and national ones. I don't track or AX.
Do some cars fail..yes. P-cars do too. But I could tell you the story of my unreliable rust bucket Honda Civic. You hear lots from those whose cars failed, and I think louder because of the intensity of feelings we have for the car.
In this uncertain economic climate, if I were in your shoes (having to be concerned over a repair bill, as you said) I'd buy neither car. I'd hunker down and save my money and drive the car I had. Once the college bills have been paid, then give yourself the treat. But I'm a conservative with money sort and that may not suit you.
Whatever you do, I hope you enjoy the result.
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