How far is to far gone?

I think the point is that he has an attachment to the car and that is why he is asking here. I understand we rarely end with a car worth what we have in it, but how many times the cars worth do we bury ourselves. I try to assess this every time, but then again I can do all the work. I am not paying labor.
Perhaps more information is needed? Are we talking a 340 4-spd triple black car w/factory sun roof? Or a /6 column shifter gold on gold? Are you motivated to maybe spend 30k or more on a 5-10k car?