Hello, Although I don't have any direct info on Jacob Bailey, I do have Jacob Bailey's in my family from Maine.They were originally from Hanover, PA and came to Maine.My grt. grt. grandmother was a Bailey who married an Indian.His father was an Indian medicine man in Lowell, MA. The name Bailey is also very common among the Indians of New England and another difficult name to trace. However him being an Officer I doubt he was Indian, but just wanted to include that in case it was any sort of a help to you.
I will go back and re-check my Jacob Bailey's and come back here and post what I have. I don't know that they are the one you are looking for, but it might be as I don't know the Military History of my Bailey family, if there was one that is.Mine all settled in Harpswell, Cumberland Co., Maine and lived there for generations.Some are still living there. I'll be back to post what I have.