Shane lives in South Dakota and found himself bidding on an old Caddy, the car performs as expected for a winning price of about $100 and now he is looking to spend a tad more on a piece of American iron with a V8 under the hood. What car should he buy?

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Here is the scenario.

A few months ago, I went with my friend to a ranch auction in northeast Wyoming. While I was originally planning on just helping him look for a tractor and some pipe for a cattle fence, I soon found myself the only bidder on a fine piece of luxurious American iron, and paid a whopping $108 for a 1999 Cadillac DeVille. It was not running when I bought it, but fortunately it was on top of a hill, so we channeled our inner trailer park boys and pushed it down the slope in neutral onto the trailer. I soon got it fired up, and although I have thoroughly enjoyed getting under the hood, impressing the ladies, and hooning on gravel roads while pretending I’m Boss Hogg, the infamous Northstar head gasket and cooling system problems have gotten significantly worse in the last few weeks, and I have painfully decided that my Cadillac needs to be put out to pasture permanently. Oh yeah, and the battery died and messed up the security system so now the alarm goes off every time I open a door, so my new neighbors at the apartment complex I just moved into already don’t like me. My employer provides a company truck, so this will be strictly a fun vehicle. I don’t mind a little work, and would actually prefer a car that requires a couple weekends of wrenching. Since I already have the company pickup and am allow to drive it for personal use, I want a car instead of a truck, SUV or crossover (I hate crossovers, by the way. They’re stupid). I would prefer a big American sedan, (Caprice, Crown Vic) but am open to suggestions. I can push my budget up to $5k

Quick Facts:

Up to $5,000

Sioux Falls, SD

Yes

Sedan, V8, ideally RWD

A crossover

Expert 1: Tom McParland - Go With A Clean Caddy

Well Shane, despite the problems it certainly seems like you got your money’s worth out of that Caddy for a hundred bucks. Since you already have some experience tackling most of the issues found in those models, it may be wise to target a nicer version of the same car. Outside of the auctions what you are mostly going to run into within this market for a sub $5,000 car is either a private sale or a questionable used car lot.

While I wasn’t able to find anything that seemed compelling in your local Craigslist, a wider net search did reveal this pretty nice. Usually, when a large dealer gets a twenty-year-old car on a trade, they tend to toss it to the auction, so the fact that they kept it could be a good sign. Overall it seems very clean and has a consistent service history. You also be hard-pressed to find anything similar in this price range with under 100,000 miles. This clean Caddy could be your ticket to cruise in style.

Expert 2: Erin Marquis - Hail Victoria

You’re open to a Crown Vic? Well, that’s all you had to say, my friend. Crown Vics continue to be bulletproof heavies of the American V8 used market, and there happens to be a fantastic example well within your price range and in your state!

This , with only 70,000 miles on it. For a mortal car from 1987, that may be a lot of miles, but this is the Crown Vic. They made cop cars out of these for a reason.

It doesn’t sound like it needs a ton of work either, maybe just a little TLC. These Vics came with a Windsor V8 Engine which put out a pretty scrawny 157 horsepower in this era, but we all know driving slow cars fast is where it is at. Plus, since the Windsor was the engine that brought Ford a ton of success, there’s still to this day a booming aftermarket. These Vics were both common and easy to work on, so breathing life into this old hunk of Detroit steel shouldn’t be too difficult.

Expert 3: Andy Kalmowitz - Be A Master Of The Road

Shane, baby, how’s ya doin’? I’ve cooked up something extra special for you on this week’s What Car Should You Buy. Buddy, what you need is a Buick Roadmaster. It’s time for you to grab life by the horns and cruise down the road in what is basically a couch with a V8 bolted to the front of it.

So far, every suggestion you’ve gotten has been good, but you deserve better than good, Shane. Don’t you think so? Better than good is a Roadmaster, my friend. With your $5,000 budget, the sky is pretty much the limit when it comes to these cars, but you’re going to have to look. Unfortunately, most Roadmasters have returned to the earth at this point, taking their pillowy seats and 5.7-liter GM V8s with them. It’s a damn shame if you ask me.

Don’t worry, my friend, because . Now, you’ve got to bear with me, because it’s gonna take a little vision on your part. What we’ve got here is a 1996 Roadmaster, the final model year. It may not look too hot (the wheels are doing it no favors), but it costs just $2,900. That’ll leave you plenty of cash to get this thing up to snuff. Plus, it has just 165,000 miles on the clock, but these things are built like tanks, so that’s barely break-in miles.

Shane, all the suggestions you’ve gotten today are correct, but this is the most correct one. Make the right choice, or else.

Expert 4: Bradley Brownell - Be A ‘Vette Guy

Every red-blooded American in history has wanted to drive a Corvette. That’s pure fact. You either have a Corvette or you want one. Why deny yourself another day? This one is for sale in Dell Rapids, SD, and it even comes in red with polished salad-shooter wheels. Being a 1993 model, this has the 300-horsepower LT1 engine under the hood, that is the good one. Unfortunately, it’s saddled with an automatic transmission, but for this budget, you can’t really get choosy.

Now, about that budget. price. Now, the ad doesn’t say anything about that price being ‘firm’ or the seller disallowing any ‘lowballers’ from contacting them. Show up with fifty crisp fresh American 100 dollarydoo notes, and you’ll probably drive away in your new-to-you C4-generation ‘Vette.

You say you want a big American sedan, and I get it, but you’ll have a sensible everyday driver, so you should definitely buy an impractical two-seat sports car as your second car. This American badass only has 152,000 miles on the odometer, and you can bet it’ll run damn well forever without so much as an oil change. (This is lightly satirical, please change the oil in recommended intervals.)

The Roadmaster Andy recommended above has the right engine, but imagine that same engine in a car weighing around 1,000 fewer pounds. Man, it’ll be a riot!