Patrick, what a fantastic Waldo puzzle! I love all things Waldo, and can tell you lots of Waldo stories...planning to talk you ear off right now about my ancestors:
I cracked it, but it took all day. I'm going to lay this out, and see if you can crack it, too. I had two red-hot working theories: the "Chip off ye olde block" theory and the "Holistic Chippewa Doctor John" theory. Everyone having anything to do with this was living near Bridgeport, Harrison, (W) Virginia.
I looked up "Chip" and it is said to be a nickname for a Junior, as in a "Chip off the old block." It can also be a nickname for Charles or Richard or Christopher, but there are no known Waldo of those names in the area.
John Waldo, Sr. was born 1728 in Windham, CT., and moved to West Virginia where he had lots of descendants in vicinity of Harrison County, luckily most too recently born to qualify as a "Chippy.". He did have a son John Jr. (a chip off the old block) and also a son "Phipps," an unusual name that sounds a bit like "Chippy" which is a very unusual name for a Will. Only the younger John Waldo (Jr.) is in the right time and place.His brother Phipps died too early, but there was a second Phipps Waldo, he is John Jr.'s son!
The first Phipps died in the Revolutionary War and John Waldo Sr. died too early. Our lives are just dull compared to these early Waldos.
John J. Waldo, Jr. survived his service as a minuteman in the Rev. War and named his first child after his fallen brother Phipps Waldo.
This second Phipps is the correct age and correctly located to be a possibility for "Chippy" Waldo.
In the following Ancestry "message board" the younger Phipps is listed as an Appraiser in the will of Lawson Riley in September of 1820, so this shows he was a person trusted with assisting in the final resolution of at least one person's estate. However, also listed here is Rev. John J Waldo (Jr.), a Baptist Reverend, who officiated in the marriages of a number of Carders and Goldens of that time and place. Meaning he was assisting in the evolution of your family, Patrick (once inside the link you can use "control F" to search for on "Waldo"):
In addition to being a respectable Reverend, John Waldo Jr. was a holistic healer who was said to have learned his craft when captured by Indians as a young man. It is unclear who captured him, but living in New York had put him close to the Chippewa territory which then stretch very far across the Northern shores of the Great lakes, a vast territory called Turtle Island by some. John Waldo Jr. actually practiced medicine on real people as well as religion. If he indeed learned Chippewa medicine, then "Chippy" could refer to such a life altering time as both prisoner and student. If the story about him being captured is false and he practiced Indian Medicine while going by the swanky name of Chippy to lend credibility to a charlatan perversity, that would qualify him a real screaming troublemaker. But I have to say this branch of Waldos tended to be pretty straightlaced.
best bio of John J Jr: https://www.geni.com/people/John-Waldo-Jr/6000000001044574266
These are my greatgggggguncle John Waldo Sr. and my cousins, but despite familial piety I was ready to give it up..... Then I notice Family Search has the West Virginia Will books online. So one last sleepy round leads me full circle to Uriah Carder's Will which was written in a very formal style and beautiful curvaceous script. I walked all day in a huge circle, but let me show you the solution which if you have read this far, you should see it if you go back to study the actual Will with my narrative in mind. I hope you have one of those free Family Search accounts like I have. For some reason I can't get my screenshot of the Will loaded here. Hope you can pull up the source and look close:
p.s. Some of these Waldos have Wiki-profiles, but I will give your grggrandfather's true friend one soon. Old friends are Golden.
p.s.s. need another hint? Contemplate orthography and calligraphy. Put the words "Phipps" and "Chippy" next to each other and trace the outlines. Then blur your eyes.