I don't have any new information for you on your O'Briens but I just had to comment on the fact that my gggrandparents also went to PEI from Ireland and settled on Lot 57 just 2 lots away from yours. Their name was Brennan and they were there in the 1840's also. I guess we will never know what hardships those people indured and overcame!
Have a nice day,
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