Lets say you get paid perhaps $100 off the books cash for a small project. Is it morally OK to not report it, but donate it in total and not take the deduction?
I think it’s moral if you don’t report any cash you receive in payment, period. So maybe I’m not the right person to ask about this. . .
It seems morally okey-dokey to me. Who in the world would benefit from you reporting it? It’s just more paperwork for you and perhaps a bureaucratic headache for someone else.
Nope. First of all, you may not be allowed to deduct the full amount if you donated it. If you don’t itemize, for example. In that case, you have illegally (and, arguably, immorally) lessened the amount of taxes you have to pay.
Second (and a much inferior argument), to whom are you donating the money? We, via the guvmint, have established categories of organizations that we recognize as charities worthy of support through charitable deductions. If you are donating without telling the guvmint, you may be cheating us by donating to the John Birch Society (nondeductible) instead of the Aren’t Kids Great and Don’t You Want to Give them Money Society.
Sua
You misspelled The Send kaylasdad99’s Daughter to Harvard in 2014 Project*. 
*also nondeductible, btw
Um, wouldn’t it just be easier to call it the “Send Kayla to Harvard in 2014 Project”?