Low mileage 74 AMC Javelin AMX, needed tires and brakes, practically free. Still couldn't afford it at 20 years old with a wife and kid

I test drove a couple Mercedes 190e 2.3-16 back in mid 2000s. could have had one for $4500. Value is now about triple. If I sell the box I might try to find a benz... or buy back my old S4.

http://germancarsforsaleblog.com/wp-...a0_600x450.jpg

A Series I E-Type Jaguar coupe in 1981 when I bought a brand new 1981 Mazda RX-7.

Any old Ferrari that was available for $5,000-$6,000 in the early 1970's that now sell for big bucks. But $5,000-$6,000 in the early 1970's was big bucks for me that I didn't have!

In the early '60's there was a real C Type Jaguar parked on the street in Cleveland with a "4 Sale" sign taped on it @ $3500.
In the late '60's there was a Vignalle Ferrari 250 Mexico @ $6000
Both were old, tired, non-competitive race cars, both achingly beautiful, both worth well over 1mm today.
In the mid-70's I passed on an original series Shelby GT 350 for $10k which I felt was over priced.
So, in 2014 I didn't let the 2000 Boxster slip away and I love it. Have put many more happy miles on it in 3+ years than I ever would have with any of the above dream cars, though I would have made lots of $$ on any of those.
Larry the Bald Eagle

A real 1970 Chevelle SS LS6 4 speed back in 1996 for $10K. I didn't buy it because it was a faded gold color. I probably could of buffed it out and flipped it for $15k at the time.

1986 930 for $24k, just a few years ago. owner was desperate to sell but i'd just bought something else and didn't have the $. appreciated 4x in the past five years. fyi, didn't enjoy the test drive; sit bolt upright, windshield in your face, pedals felt odd compared to the boxster.

funny this thread came up, as i am anguishing over buying a 1969 triumph gt6 that has been a race car since birth but is still road legal. fully built engine, no rust, turn-key vintage racer for $10k. i shouldn't but i know i will regret it if i don't.

Back in 1986 I had all the paper work and loan done for a new ACS McLaren Capri and decided at the last minute not to buy it. Ended up buying a Mustang SVO that turned out to be a pile of junk.

http://www.cantweightclassics.com/fi...McLaren/06.jpg

I had a '69 (I think?) bmw 1600 as a project car that never got off the ground. Finally traded it for an actually running '72 2002. That was a great car!

BMW 316 in 1975. We were worried that car sales taxes would go up and BMW didn't have any inventory, so we bought the worst car we have ever owned instead, Austin Princess. And the taxes did not go up!

While shopping for my first car in 1978 I looked at (and drove) both a 1972 911s and a 1967 Austin Healey 3000. Both were, unfortunately, outside my budget at around $AUD11,000 and $AUD4,000 respectively. I ended up with a $AUD700 1964 VW Beetle!

Then in 1994 my then GF's grandfather passed away and I had the choice of either (or both) a 1973 Mach 1 Mustang or a 1973 Ford Landau - both with the Cleveland 351 V8 in immaculate condition and VERY low mileage. He loved polishing them, looking at them and driving them JUST enough to keep them healthy. Oh, and he had owned them from new!

His wife (not grandmother) was asking $AUD5,000 each for them but for some bizarre reason I thought my Toyota Camry was a much more sensible option - idiot!

For those of you that may not be familiar with the Aussie version of this muscle car, here is an image of a good example of a Landau...

http://986forum.com/forums/uploads02...1512611467.jpg

Here is my 1970 T/A I did buy in 1990 for $5,500 best deal I ever made, had 73,K miles when I bought it. I had previously bought one for $500 that needed the engine rebuilt. I parted it out because it had a little rust in the floor panel. I should have restored it.



http://986forum.com/forums/uploads02...1512613113.jpg

A clean no-rust all original 240z from California for $2k in 2013. I bought a 2000 Dinan supercharged BMW E38 740il instead and regretted it ever since haha.

That is very rare car (the GT6). It's also an excellent price if the condition is as good as you say. A friend of mine had one that he restored; a fun beast!

A GTO Judge for 2 grand in 1978. Actually, my dad would not let me buy it. I was 16.

In 1990 I had a '57 Triumph TR-3 that was rough and I wanted something a bit nicer. I found a nice red '62 or so Alfa Romeo Giulietta Spider that the owner wanted $6k for. That would have been a big stretch for me, so I passed. I bought a freshly painted '74 Spitfire that I drove for year or so, found that the frame was rusting from the inside out and dumped for a bit less than I paid for it. The Alfa would have been a keeper. I got a nice Alfa Spider (Euro'd out '80 S2 that had a built engine and suspension) about ten years ago. Yes, every car guy should have an Alfa at some point. They are definitely special. I sold mine when I got my Boxster S. The Boxster is a better car in every way except I still find myself missing the Alfa for some reason...

1967 Alfa Giulia Sprint later called a GTV
 

A few weeks after I got my first professionl job in 1976. 60k, White on tan interior. New Michelins. Perfect condition. $2000. Had to borrow some $$ from my dad. Came back 4hours later.... sold. Was so crushed that I lost it, I bought the very next one to hit the market in the Bay Area. A ratty example that I bought for $1600, without test driving on the freeway. Howling differential I discovered driving home after purchasing....

The car that I regret not buying the most is a brand new 1969 Beaumont SS 396 4 speed convertible. I still think about it today.

In 1972 had the chance to buy a 1961 Austin Healey bigeye for $600.00. My Dad
Talked me out of buying it cuz $600 for an old used car was crazy....

A 1960 Bugeye Sprite was my first car in 1973. I paid $800 for mine and more or less broke even when I sold it, replacing the rear axle twice, rebuilding the engine and some other repairs over the two years I owned it!

1959 Porsche 356 Convertible D in 1974. I think the asking price was $1400. Like BFeller, my Dad wouldn't let me buy it. (Actually he said I couldn't keep it at the house while I worked on it.) His concern was that I would get involved with car and not go to college. He was right. I think I lacked impulse control at the time.

Not my car (obviously) but it looked like this - only a lot rougher.