If you're thinking of flipping or selling the car, it doesn't make a lot of sense to paint it, you'll never get your money back out of it.

If you're painting the car because you want to fix it up and keep driving it, it makes a lot more sense to do it. I have a POS BMW station wagon that's pretty rough and I'm on the fence of whether to paint it or just keep driving it as-is. It isn't a show car, I'm not planning on flipping it, it's just a daily driver for me. Would sure look good painted though. So I understand the struggle. If the money were available and it's just for me, I'd do it no question.

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Current stable:
1995 E320 157K (Nancy)
1983 500SL 125K (SLoL)

Gone but not forgotten:
1986 300SDL (RIP)
1991 350SD
1991 560SEL
1990 560SEL
1986 500SEL Euro (Rusted to nothing at 47K!)

Gone and wanting to forget:
1985 524TD 167K (TotalDumpster™) [Definitely NOT a Benz]