Here is an off the wall approach to your part. This example is using an end mill with a 45 degree chamfer on it that is custom made, this company makes excellent form tools, AB Tools, Inc. | Carbide Cutting Tools and Milling Tools (abtoolsinc.com). The attached sample has a 45 degree chamfering edge on it, you should be able to get a radius edge created also. By using mill bore, you can select all the holes at once, and you control how much of a chamfer you want by controlling the depth. One consideration to make of course is cycle time. Your drilling process might be faster, but programing might take longer, you will have to make that determination on your own.
Regarding the form tool, you might even be able to have the tool made with a drill point. Use the form tool to first drill all the holes, leaving a small amount on side walls, then use bore to finish the holes. On the bore cycle, you could cheat and not start at the top of the hole but maybe .100" or so from the bottom to make the cycle shorter. Just an idea.
Leo C