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At this point a 1997-2000 Boxster costs the same or really less to own as a new 25,000 car. People worry about the maintenance costs when forgetting about the depreciation costs.
All cars depreciate about 10-15% per year. So a car costing 25K will go down about 2500-3500 in value in a year and add in 200 maintenance.
An early Boxster costs now about 10-12K. Over the last year prices have stopped falling. They are getting so close to parts value that they may not drop further. So let's say about 500-1000 depreciation per year plus maintenance of 1500-2000 per year.
It's highly likely to cost you less to own a Boxster and the Boxster even has a chance in 15 years of going up in value whereas the new car has no chance.
Of course the Boxster has a chance of dying but that's where the 1.5-2k per years goes - it can be used to maintain and restore the car and worst case you can sell it as a roller and still be ahead.
Now this analysis doesn't work for 20-45k Boxsters that are newer.
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