So solutions are:
1: Band aid it with caulking and flashing and hope that it works. Probably wont and will risk tons of bad damage later:
2: Spend 3-5K additional on materials and cut a 6 inch wide, 4 inch deep channel into the concrete and install channel grating to drain the water to the downspout title...
Obviously I'm going with the cry once approach and fixing it right. I hate cutting the concrete but no choice. Then we will still caulk it once it dries out and flashing will be installed to help mitigate any potential overflows.