Although my needs should come after the needy, when I make a charitable donation, I prefer to get a tax benefit, and donations of my miles do not confer any tax benefit. Better to give away apprecitated stock or even cash than non-deductible miles.

The plan to convince DL to make the gift is, IMO, far better than the OP donating miles (or tickets obtained with the OP's miles). In years past, I arranged donations of tickets to charitable fundraisers. The best came from local station managers of NW.