So…it’s not going to be a Gambler car. Instead, I’m restoring it to its former glory. This car has only 100,000 miles on it, and I believe its best years are still ahead of it. This car will appear in a build series I’m launching as well as another piece I’m writing about the pain and expense of keeping an old Volkswagen’s heart beating, sometimes using parts of other Volkswagens. Just last weekend I found myself racing against the clock to plug the car’s various water leaks before the first snow of the season.

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2008 Smart Fortwo Passion Coupe

2008 Smart Fortwo Passion Coupe

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Photo: Mercedes Streeter

This $1,000 Smart Fortwo is the replacement for a 2005 Fortwo Cabriolet I bought in 2018 and sold this year after it became a major lemon. This car was slated to become a dedicated off-road build. I did run one off-road rally with it, but I have decided to change the car’s fate. Instead, I will make this car into a creation inspired by a Volkswagen Harlequin Golf.

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16 / 18

1997 International 3800 School Bus

1997 International 3800 School Bus

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Photo: Mercedes Streeter

This one’s a bit left field, even for me. I’ll level with you when I say I enjoy RVs. However, I don’t enjoy how they’re built. Think of them as needing the repairs of a car while also needing the repairs of the worst house ever built.

I’ve been looking for specific kinds of RVs since 2014. I long wanted a bus, but never thought I could ever own one. So I instead chased vintage fiberglass campers.

My girlfriend gave me this bus for my birthday and we’ve already started tearing apart the interior to make a camper out of it. The idea is that the rear end will be a motorcycle garage while the rest will be living space. It’ll be a dry camper at first, with running water coming later. For those of you in love with commercial vehicles, it has a DT466E with an Allison AT545 transmission. Not the best transmission out there, but it’ll be fine for out here in the flat Midwest. This will also be another build series of mine as well!

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17 / 18

2006 Ford E-350 6.0 Powerstroke

2006 Ford E-350 6.0 Powerstroke

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Photo: Mercedes Streeter

To round out this list is my Gambler 500 vehicle. This vehicle is usually on a rotation. I’ll drive it for a month or a few, then sell it and move on to another vehicle I’m interested in. For this winter session Gambler 500 runs I decided I wanted a van. We plan on keeping this van as long as possible because it’s so much fun with so much space. This gives us a good place to lay our heads in the winter that’ll be easier to keep warm (hopefully) than a tent. And because I’m me, I wanted the van to be something special. So for $700, I got this 6.0 Powerstroke.

The funny thing about most of these vehicles is that most of them were had for $1,500 or less, with a whole bunch of them under $1,000. I’ve turned buying and selling sub-$1,000 vehicles into a sort of art, and sometimes I’ve found absolute gems by doing this. And yes, all of them run!

Over the next indefinitely through space-time I will expose you to the wacky everyday adventures of my vehicular enthusiasm with regular doses of rare vehicle finds, large vehicles you most definitely should purchase and what vehicle I’m off-roading each week.

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