As a 25 year cigar smoker and recent convert to pipes, I have really enjoyed C&D Habana Daydream which you can get in bulk. I did score a 4 year old tin so that may have something to do with it, but I've found it to be a very nicely balanced blend with no bite. I also like to use burley and cigar leaf to cut aromatics and Englishes to make them a little more to my tastes. Burley tends to agree with my cigar-loving mouth. Virginias smoke very hot to me.
Your dad also might like something like Sutliff J4 burley or Sutliff 79 mixed with a bit of cigar leaf.
Thanks! This is more in line with what I’m looking for. Solid advice from @mortonbriar and @shermnatman but if I’m trying to get him to explore pipe tobacco, cutting up a cigar and stuffing it into a pipe is only going to have him thinking it’s not worth his time. Just my opinion, but I know the old man and how he is.
I’ll grab a few of these tins, along with Winchester, between now and when he gets here and then report back.