The $5,000 Challenge, you don’t see that every day edition part three

The biggest complaint we hear about new cars from mainstream manufacturers these days is this: Thanks to current crash-testing and fuel economy regulations, they all look the same. Perhaps what Hemmings readers are really objecting to is conformity, since the second-most common complaint is that all of today’s cars are silver, gray, or black.

Every single vehicle in this $5,000 Challenge is guaranteed to stand out in a crowd, and there isn’t a silver one in the bunch. All, we suppose, are acquired tastes, and some will require a bit of effort (and sums of cash) to turn into daily or weekend drivers. Does the end justify the means (or the elbow grease)? That’s for you to decide.

1989 Dodge Dakota convertible

Americans love pickup trucks, and Americans (in warmer climates, anyway) also love convertibles. Combining the two was not a new idea, but when Dodge launched its Dakota convertible pickup in 1989, it targeted a segment that had been largely untapped since the 1930s. Consumers soon pointed out why, buying less than 3,500 examples in the model’s three years on the market. That makes them a rare (but practical) beast today, and this example, though high in mileage, appears to be in good condition. The asking price? $3,900.

1998 Cadillac DeVille hearse

To be frank, hearses don’t appeal to everyone, thanks to their morbid (but necessary) raison d’etre. For those that can look beyond this, these professional cars offer a lot of interior room (perfect for a small camper conversion or a weekend discount warehouse hauler) and tend to be good values. Most led relatively pampered lives, too, with frequent washes and servicing; after all, no funeral director wants to deal with a mechanical breakdown in the midst of a procession. This 1996 Cadillac DeVille hearse was constructed by S&S, and built upon GM’s new front-drive professional car platform. Unlike most, it’s finished in tasteful gold instead of the more traditional black, perhaps increasing its appeal. The asking price? $4,900.

1991 Alfa Romeo 164S

Built on a platform shared with the Saab 9000 and the Lancia Thema, the Alfa Romeo 164 was intended to be the Italian brand’s answer to the BMW 5 Series and the Mercedes-Benz E Class. Though relatively popular in Europe, the 164 was uncommon in the United States, thanks in part to Alfa Romeo’s small (and declining) dealer presence. In 1995, the 164 earned the dubious distinction of being the car that ushered the brand out of the U.S. market, but its departure had little to do with an individual model. This 1991 164S reportedly spent much of its life in Florida, and is said to be well-maintained. There are still a few items to address (such as the hole in the muffler and the slight leak in the rear main seal), but for the right buyer these are bonding opportunities, not flaws. The asking price? $4,750.

1966 Ford Galaxie 500XL convertible

An ancient bit of car-retailer wisdom says that, “If the top goes down, the price goes up.” The same can be said, in reverse, about displacement, meaning that as engine size increases, so does the price. Finding a big-block car under $5,000 is a rarity, but finding a drop-top big-block in this price range is rarer still. Yes, this 1966 Ford Galaxie XL 390 convertible will need lots of work, including floors, a trunk, a top, and paint, but the end result will be a particularly entertaining driver capable of hauling (and we do mean hauling) yourself and four friends in windblown bliss. The asking price for this work in progress? $4,900.

1986 Honda Big Red 250

From 1979 through 1987, Honda’s three-wheel ATCs were a go-almost-anywhere alternative to minibikes and dirt bikes. By the midpoint of the 1980s, however, both consumers and government officials were beginning to question the safety of the popular off-road vehicles, which proved somewhat less than stable when cornering at high speed or on rough surfaces. Sales were banned in 1988, leading to a new market for four-wheel ATVs and, eventually, increased collectibility of the suddenly-illegal three-wheelers. Now out of production for three-plus decades, surviving examples are scarce and increasing in value. This 1986 Honda 250cc “Big Red” ATC looks to be in decent overall condition, suitable for use around the farm or on the local trails. It appears to be a reasonable candidate for restoration, too, and chances are good its value won’t go anywhere but up. The asking price? $2,500.