The most I ever paid a month for a car was $465. When wife #1 left me, I gave her the car (and the payment) in exchange for the house and mortgage ($300/mo.)

I'm paying $350/mo. now for a used 2002 Jeep I bought in 2006. This car is the boss's car, I only drive it with her permission, or when she needs a chauffeur.
As far as the rest of my "fleet" goes, all are paid for, and most were bought for less than $600. All have over 200,000 miles and all run very well (Except the Olds. Anybody know where I can get a 1985 or so MFI 2.8L V-6?)
I have a 1993 Buick and a 1980 Malibu, both of which I got for free and both of which I use for mail delivery and daily drivers. Both have over 200,000 miles on them. I just finished rebuilding the transmission in the Malibu. (I'm looking for a replacement tranny for it. Turbo 350, 4L60, or 700R4, anything to replace this POS Turbo 200!)
I have a 1988 Ford F-250 diesel with over 250,000 miles that is getting a "facelift" (sandblasting and repainting the frame and cab, replacing the fuel injector pump, thanks to ULSD fuel, and new seals and gaskets on the engine, transmission, and drivetrain)
I have a 1995 Chevy S-10 Blazer with 235,000 miles that will be my backup delivery vehicle for when the snow gets deep. I got it real cheap, ($100) cuz the owner thought the engine was shot. Every time they put water in it, it would run out as fast as it went in. $3.00 worth of freeze plugs fixed it.
I have a 1985 Oldsmobile Firenza that I've converted to right-hand drive, but it needs a motor.