Okay, let's play this game again. What car?

Okay, here's the criteria:

Must live outside in Florida.
People must look at it and say: "That's a classic car."
Must be fun or entertaining in some way. I don't care which way. Just justify its fun factor to me.
$3000 budget cap.

GO!

Oh, and reliability, practicality, ease of repair–those are all meaningless to me.

Rambler is the answer---- cheap, classic, dead-nuts simple, and the AMO is a great resource. You won't find many choices for classic cars under $3K--- but you'll find Ramblers---- and maybe an old ratty Beetle--- but rust will be an issue with the VW at that price.

http://atlanta.craigslist.org/atl/cto/4681610287.html

In reply to captdownshift:

Take off that single bumper overrider, and I'd say you are very close to a winner!

Freakin sweet.

The answer to this thread already has its own sub forum here. its the 2014 classifieds...

Considering there are at least 4(!!) of these vw-kit TDs on miami CL right now, I bet you could get this for 3K (listed at 3500, plus its also mis-listed as a Midget, so they might not be getting many bites):

CL Link

TJ with 5.9 Magnum http://jacksonville.craigslist.org/cto/4674459575.html

Ok.. A real suggestion http://daytona.craigslist.org/cto/4620536283.html "no iam not the original owner and no its not stock it's a death trap a car you don't have to worry if your drunk ass girlfriend hits something with your door as she opens it to puke her guts out"

Yes. My search term was "death trap"

$3k makes it a bit more difficult but standard answers apply: Miata, MR2, RX7. But I think you'd really have to go '80's probably to get any kind of decent car for that. Maybe '80's Mustangs, Firebirds, Camaros, plus something '70's like a Pinto or Vega if you can find one. Personally, I'd probably be looking for a B210 fastback, TR7 or something similar. But again, finding one can be problematic. Or better yet, a LeCar! Nothing says I'm upper management material than pulling into your work parking spot like a LeCar!

However, my overall number one pick would be a Fiat X1/9. They are available at that price if you hunt for one, and truthfully, there are few cars that drive as good, even today.

1973 hilux http://orlando.craigslist.org/cto/4693517689.html

I just did a quick search, and at least around here (North Alabama), you can get many Alfa Spiders at or near your price. There's even a nice looking chrome bumper '74 for only around $4k, or a rougher looking Graduate for $2.5K.

GLH!!

Look at my avatar. You want one.

Sunbeam Alpine... Complete with racing stripe.

http://denver.craigslist.org/cto/4678452370.html

Keep thinking Italian or French...walking is good for you!

a sandrail of dubious construction with a 500Ci Caddy.

http://jacksonville.craigslist.org/cto/4683046296.html

Drug dealers car http://jacksonville.craigslist.org/cto/4691705275.html

Jag xj6 with lots o' parts

http://denver.craigslist.org/cto/4619231670.html

alfa 164L http://jacksonville.craigslist.org/cto/4644062577.html

'66 Chevy Malibu http://denver.craigslist.org/cto/4633538747.html

Fiat 124 with diesel engine http://lakeland.craigslist.org/cto/4679798264.html

In 20 days I hope to convince you that the answer is Infiniti Q45.
Finding your own is pretty easy:
http://daytona.craigslist.org/cto/4680907859.html
http://miami.craigslist.org/brw/cto/4656452727.html
http://miami.craigslist.org/mdc/cto/4608886370.html

Staying with Nissan, many of the middle year Z-Cars are bargain priced. Ample supply with good parts sources but not yet climbing fast in price but a Classic look.
Sample: '87 300zx

Tom Suddard wrote: Oh, and reliability, practicality, ease of repair–those are all meaningless to me.

With this above statement included then the answers should be:
Lancia or Opel

How about a Jaguar XK8 coupe with 200k miles.

Anyone of the Bugatti's I saw a couple weeks ago at Keene NY.

You could pick up one of these for that:

They are pretty much classic status now. Everyone seems to like them.

Mitsubishi Starion Chrysler Conquest

Unlike some other cars here you can pick up a decent to good one for that.

They handle good, have wide wheels stock to fit a lot of tire, and have a lot of options if you want more power and handling. BTW keep the stock wheels for them. They are awesome.

This site pretty much covers all aftermarket upgrade needs: http://www.racetep.com/dod_mit.html

Here's a recently semi-restored one with performance parts for $1300 http://miami.craigslist.org/mdc/cto/4689010821.html

http://atlanta.craigslist.org/wat/cto/4684308188.html

Corvair? Under 3K is really tough.

NM the corvair...Vintage race this bad boy.

http://atlanta.craigslist.org/atl/cto/4684174868.html