I have thought about a similar move. You will be spending more to get a Macan of course as an '08 Jeep and a '99 Boxster are probably worth less than half of a Macan. The Macan is still depreciating and a compromise in sportiness however.
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'58 356A coupe, just a driver
'00 Boxster S fair weather - daily driver
'11 Jeep Grand Cherokee Limited - winter daily driver
'92 F250 - junk hauler; previous Porsches '95 993;'08 Cayman S;'70 911E
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