In my random fantasy searches yes I am bumping into early Boxster's in the $5K range... but yeah they are pretty worn. (and buying a car that needs a bunch of work is NOT my idea of 'fun')

If/when I'm ready for a fun car I will start with $10K and see what is out there... and that brings a couple other Porsche's into the picture (996).

A $10K Boxster will be nice. A $10K 996...not so much.

I bought a 2001 Boxster last summer for $11K with decent miles (6x,xxx), lots of records and the IMSB done. I bought it to drive to the Porsche Parade in Vermont (3,000 miles worth of driving). Absolutely zero issues so far.

You probably won't get that for a $10K 996. For that kind of 996 you'll be closer to $20K....

A quick search and yes, you are correct, a decent 996 will run $20K

But I have some criteria:
I'm turning 60 in a few months and retiring (i.e. getting rid of the appliance commuter car and getting a fun car) in two years so 996's will have come down a bit by then.

As much as I love the top down experience my ownership of the Miata cured me of that (blond, blue-eyed, balding, middle age dude doesn't need the sun beating down on his head,)

And I'm noting Cayman's are dipping into the $20K range (however at +60 I may be more into a GT ride than a sports car).

Sorry for the hijack... back to Boxster prices.

I think Boxster prices will bottom out at about $10k or so, you're really hitting about rock bottom for even a basic transportation appliance. The 996 will always be more because it's a 911. So I doubt you'll ever see a decent 996 for $10k.