John, your eye and knowledge of postal history are impeccable, thanks for taking time to look and provide input. Unfortunately the cover itself has some browning on it. Not sure if it's from improper non archival material it was stored in. When I pulled these covers from the "Family box" I moved them into big manila envelopes and stored them in a rubbermaid container. All in all I had roughly a dozen of these manila envelopes crammed with covers and separated by decades. Still, since the cover is 104 years old I'm not going to lift the stamp.
A couple more I thought worth keeping.
I believe this one was mailed to the Chicago State street address then re-routed to New Haven VT. To me this makes sense since my family did own the property at 1406 N. State street but moved to New Haven. The recipient is my grand mother and my Mother was just a young lass when they moved to New Haven. I think the postage due is the double deficiency fee.

This one I didn't bin because I've never see the auxiliary marking of the 75¼ before and not sure what it means.
