Are the following sentences natural to a native ear?
1. I would have been damned if I had not reached up to here.
2. You would be damned if you didn't finish college, given the history of your family.
3. That is an equivalent of you throwing money away.
1 reached up to here- unclear what you mean, but, is it something like had not got this far?
3 I'd use That is the same as/exactly like throwing money away.