My newest vehicle is a '79 GMC pickup. This is my primary driver. In 21 years of driving, the newest vehicle I've used as personal transportation was 10 years old.
Whenever I get a new addition to the fleet, I pretty much run down my standard list of things to examine and replace. This list includes every last rubber component on the engine. I also do a really thorough job of repairing all the things prior owners have neglected.
I spend a bit of time ensuring both normal and emergency brake systems are top notch.
I won't bore you with the details of exactly what I do, but I second the AAA idea. I also carry a small tool kit and extinguisher in each vehicle.
Driving an older car defensively will more than compensate for a lack of ABS, traction control, or any other modern gee-whiz technology. Especially in my truck, you cannot get away with tailgating especially in damp conditions.
The biggest hassle I think you'll have to overcome is water and wind leaks due to worn weatherstripping. Reliability issues due to the accumulation of neglect. And, the lack of modern amenities such as cup holders and seat warmers for your sig. other.
I recently was in the market for a pickup, and after suffering mild sticker shock at the price of new vehicles and the depreciation, I looked at an older truck. While not fancy or tricked out, I've got reliable transportation for 1/10th the price of a new truck. Plus, any repairs or maintenance needed can be accomplished in my driveway.
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"I work in high speed aluminum tubing."
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