Hello Todd
I wonder if in your research of your Hilary line (...his wife (Ann HELAY/HILARY)), if you have come accross a marriage with a female Hillary and a male Douglas?
My Douglas line comes from the Lurgan area (some of the family settling in Kinnego, which is next door to Clanrolla). The name 'Hillary" is a name that carried forward for a few generations, as the first name of boys. I have a theory that there was a marraige early 1700's (or late 16oo's) that would have resulted in the name given to the boys (there was a Hillary Douglas, for instance, that was a freeholder in Kinnego).
In 1726, there is a William Douglas, listed as a weaver, living in Clanroll, 10 years later he is in Lisacorran. In Clanrolla, there is a Henry Hillary, farmer, in Clanrolla (1735).
(Thank you, Andy, for everything that you have shared on your site)
Jenni