I thought this story was “lost forever” so to speak as I originally published this way back in 2015 on a now defunct platform. Somehow, I ran across this old tale and thought it was worth sharing again. 

I’ve had a number of automotive missteps in my life, for example, when I bought my 1997 Porsche Boxster. No, no, the Boxster itself was really a great car, I kept it for eight years and had basically no problems during that time. It was reliable and incredibly fun to toss around. The misstep there was that I had always wanted Porsche 911. I chose to go with a Boxster since I had just moved to California and I thought if I was ever going to own a convertible then this was the time to do it. I could enjoy it a few years, sell it, then buy my 911. That was in 2010, within three or four years of buying the Boxster prices for classic cars started spiraling out of control. That affordable $12,000 air-cooled 911 was suddenly a $40,000 car. And they just went up from there.

The difference between this and what follows was I didn’t have a particular 911 identified, thus I wasn’t trying to decide between it or the Boxster. I had simply decided I wanted to see what it would be like to own a convertible and I didn’t care for convertible 911s, so I only looked at Boxsters. I wasn’t kicking myself because there was a particular 911 that “got away” so to speak, it was more of a general notion.

The Porsche 911 was always a dream car, but even more so was just about any Ferrari. When I bought the Boxster, I didn’t have Ferrari money, I could have stretched to pick up a good 911SC back then, that would have been $12,000 to $15,000, however the Boxster was a steal at $4,000 (and I seriously got my money’s worth out of that car). It wasn’t long after buying the Boxster that I realized there were some Ferrari’s I could afford if I dug deep into my pocketbook. I entertained that idea no less than three times and ultimately walked away all three times for various reasons. These are easily the three biggest automotive regrets of my life.

1985 Ferrari 308 GTS QV

I found this car for sale in December 2011, it was in Los Angeles and I’ve had a love affair with this particular color scheme on the 308 for decades. It was a special order color called Prugna and it was paired with a tan interior. If I was ever going to own a 308 GTS QV, this was the one. It was the perfect color, absolute concours condition with only 9,800 miles on the odometer, and it was priced at $47,000. More than I wanted to spend, but I could have made it happen.

If this was my dream 308, then why did I pass on it? In 2011, $47,000 was a steep price for a 308. In fact, concours level cars were selling for $35,000 tops, so this one was about $12,000 overpriced. This one was concours, it was perfect, and I would have forked over $35,000 in a heartbeat for it. But, back then, I couldn’t justify the extra $12,000, I thought I’d never get that back if I ever sold the car. Plus, I’d have the added expense of either shipping the car to me or buying plane tickets and driving the car back. It just didn’t make much financial sense in my head.

It should be obvious why it was a mistake to pass on this car. I didn’t have a crystal ball, so I didn’t know that a year later a 308 GTS QV in this condition would have easily fetched six figures, possibly over $200,000 if I had bought it then and sold it towards the later part of 2020 when all car prices were out of control. Today, in 2025, this would still hit six figures in the shape it was in, but an example in average condition still hits between $75,000 and $80,000. Interestingly, this car did sell and within a month showed up for sale clear across the country in New Jersey (if I recall correctly) for $76,000 at another dealer. A few months after that it showed up at yet another dealer (I think in Florida) for $84,000. I lost track of it after that as I had clearly realized my mistake.

1986 Ferrari 328 GTS

I found this car for sale locally in August 2012, it was a gorgeous blue over tan interior with 54,000 miles on the odometer. It was priced right at $35,000, which was actually about $15,000 under market value at the time. It was stunning and then a peculiar thing struck me as I looked at the car—I had encountered this car before. Much like my 308 GT4, I had seen this particular 328 out in the wild in 2008 during my accidental car week attendance. It was parked on the street in downtown Carmel, the photos you see here are a couple I shot then.

This car was beautiful, in great shape, and the price was right… so why did I pass on it? I let two things stand in the way of this, one: it was a 328 and I preferred the 308 interior by leaps and bounds. Two: I didn’t know a lot about the 328 in general, thus I let the idea of “Ferrari maintenance” cloud my judgement. You always hear stories about how unreliable Italian cars can be, and then how expensive they are to maintain. While the cost of entry was right, I was honestly scared that I may not able to maintain it properly.

Like the 308, it should be obvious why it was a mistake to pass on this car. When I was looking at the car, little did I know the 328 was one of the most reliable Ferraris made. Today, in 2025, these cars easily hit six figures, and if you have something a little less common (like one painted blue), it would likely command a premium.

1975 Ferrari 308 GT4

I found this car for sale locally in November 2012, in all fairness the 308 GT4 was always the Ferrari I wanted. The dealer was asking $25,000 for the car, and this was right when they started going up in value. If I had found this car one year earlier, it likely would have been under $20,000, closer to $15,000. This one was silver with a black interior and it was more of a driver quality car than a show car. It was missing the headrests, the interior was a little shabby, the weather seals were falling off, the antenna was missing, etc. Not a basket case by any means, but certainly needed some love. But… it was my one true love when it comes to Ferrari, and price felt right at the time. As a bonus, it was also a 1975 model which meant I didn’t need to worry about smog testing here in California.

If this was really my favorite Ferrari, and the price was reasonable, then why did I pass on it? This isn’t as big of a regret as the other two, but it’s still pretty big. It was a solid 308 GT4 that just needed a few minor cosmetics to make it a really good. But, while I’ve always wanted an “anything but red” Ferrari… silver really wasn’t the color I wanted either. I was also somewhat put off by the condition. While I wasn’t looking for concours quality, I did at least want the car to be in good shape and have all its bits and pieces, and this car was missing a lot of little things. However, if I had bought it and it turned out to not be the love-of-my-life car that I truly wanted, I could have doubled my money a year later. Today, in 2025, an example like this one would still command $50,000 to $70,000. Interestingly, this particular 308 GT4 sparked my “deep dive” into these cars. I realized when I was looking at it that I didn’t know everything to look for, I only noticed the blatantly obvious things. That was probably another reason I walked away.

In hindsight, all of these were great cars and any of them would have been a good deal. But, hindsight is 20/20 and I ultimately walked away from all of three of these for what now amounts to silly reasons. The reality is that I get attached to my cars and if I had bought any one of these, I likely never would have wanted to sell it regardless of how much profit I could have made—unless it was retirement money, but none of these were that valuable!

Needless to say I did learn from these mistakes. When I found the next Ferrari that I was serious about, I bought it. The good news is that I don’t regret that decision at all. I had learned much more about Ferrari in general, and specifically the 308 GT4 so I knew what I was looking at and promised myself I’d never make the mistake of walking away again. Of course, I got a lot more particular about what I wanted and it took a long time (nine years) to find another Ferrari that I was serious about. When that time came, it felt right, and I closed the deal instead of walking away because I was scared of the unknown or it wasn’t the right color.