Trying to trace my earliest ancestor......but struggling!

[pinefamily]

I would be looking at wills to sort out for certain the various John's in that genealogy.

[Maiden Stone]

cristeen:
I'm afraid I've implicitly trusted Ancestry Hints in the past, but will treat them with suspicion from now on!

Josephine and Maiden Stone  :
I'll renew my research of Alicia, but it is good to see her confirmed as a child of John Dakyns and Jane Okeover, with a sister Lucia.

I agree with Cristeen's post.

You mean Alicia confirmed as a child of John de la Pole and Jane Okeover.
According to 'Notices of the family of Pole or de la Pole of Derbyshire  ...'  which I cited in a previous post, Alicia de la Pole was probably the daughter of a John de la Pole of Derbyshire and Staffordshire  and Jane Okeover. The writer stated his/her opinion that it was the more likely relationship. Some other researchers had a different opinion. It's not 100% confirmation. You would need to know what sources the author used to reach the decision.
The 'Notices' seem to be a correction to information in volume VIII of 'Collectanes Topographica et Genealogica' .
I can't judge reliability of either writer. Medieval research is difficult, especially where women are concerned, as author of 'Notices' remarks.
There is information on the Daykin family in the article.

[Maiden Stone]

A tree on roegenealogy.com has Alicia de la Pole, born in Wingfield, Suffolk, parents John de la Pole and Elizabeth Plantagenet. A note says he was John de la Pole of Hartington.

Imo the note that Alicia's father was John de la Pole of Hartington is the only part of the above which is correct. The other John de la Pole was the Duke of Suffolk, married to Elizabeth Plantagenet, sister to King Edward IV. Wingfield was home of Dukes of Suffolk. Alicia de la Pole was probably born somewhere else.

[BushInn1746]

You'll need to prove who you are and where you live to get a Readers Ticket ...

de la Pole search dates 1000 to 1700
https://discovery.nationalarchives.gov.uk/results/r?_ep=de%20la%20pole&_dss=range&_sd=1000&_ed=1700&_ro=any&_st=adv

Acquired print images for a Medieval Grange building (now gone) where I live from an Index. But the Medieval writing inside one will need a specialist to even decipher the Deed.

Got two later, but Medieval documents (same building) I recognise as Latin.

There are many numerous errors re online Trees.

Re Family history, I can't get back past my ancestor born 1785 to 1786, despite tracing, acquiring extra document images (not online) and 23 newspaper references to the family, over 20 years.

The majority of family history documents acquired are not online and many are not even indexed online either. This is why family lineage histories vary in books too, as it is dependant upon how hard a person searches in manuscripts and their burden of proof threshold.

Got two books on the COBURN HOOD family (not related), one written by HOOD claiming to link to the COBURN family and one written by COBURN citing documents, Memorials and claiming that HOOD can't make the connection.

Mark

[Maiden Stone]

You'll need to prove who you are and where you live to get a Readers Ticket ...

de la Pole search dates 1000 to 1700
https://discovery.nationalarchives.gov.uk/results/r?_ep=de%20la%20pole&_dss=range&_sd=1000&_ed=1700&_ro=any&_st=adv

Before you start searching through the almost 700 catalogue entries you need to distinguish the various de la Pole/Pole families so that you know which documents to ignore. A large number of them concern the Suffolk de la Pole family; I noticed some about the Earl of Lincoln, eldest son of the Duke of Suffolk, designated heir to Richard III,  who was killed leading a rebellion against Henry VII. You may need to do some historical background reading.
Some documents in National Archives online catalogue Discovery may be in county archives.

At least 2 members of the Derbyshire & Staffordshire de la Pole families served as Members of Parliament.
John de la Pole of Hartington, Derbyshire and Alstonfield, Staffordshire was (born c. 1385) became M.P. 1416.
https://www.historyofparliamentonline.org/volume/1386-1421/member/pole-john-de-la-1385
A brief biography is included. His friend, Thomas Okeover is mentioned. Okeover was also an M.P. and had property in Derbyshire and Staffordshire. Click on Okeover's name for the entry about him.
There are probably Okeover documents in National Archives catalogue.
Peter de la Pole of Radbourne, Derbyshire and Newborough, Staffs., kinsman of the above John.
https://www.historyofparliamentonline.org/volume/1386-1421/member/pole-peter-de-la-1444
He was present at Derbyshire parliamentary elections and helped to return his kinsman, John de la Pole of Hartington.

[Maiden Stone]

You'll need to prove who you are and where you live to get a Readers Ticket ...

de la Pole search dates 1000 to 1700
https://discovery.nationalarchives.gov.uk/results/r?_ep=de%20la%20pole&_dss=range&_sd=1000&_ed=1700&_ro=any&_st=adv

Before you start searching through the almost 700 catalogue entries you need to distinguish the various de la Pole/Pole families so that you know which documents to ignore. A large number of them concern the Suffolk de la Pole family; I noticed some about the Earl of Lincoln, eldest son of the Duke of Suffolk, designated heir to Richard III,  who was killed leading a rebellion against Henry VII. You may need to do some historical background reading.
Some documents in National Archives online catalogue Discovery may be in county archives.

Results when selecting years 1400-1499 include several items at Derbyshire Record Office. Some of them are among the estate papers belonging to the Okeover family of Okeover: Staffordshire  and Derbyshire estates.
e.g. Title:  Power of attorney by John de la Pole of Hertyngton and John de Okor [Okeover]
Power of attorney by John de la Pole of Hertyngton and John de Okor, brother of Thomas de Okor,  to Geoffrey Walker to deliver seisin to Thomas de Okor of the manor of Okor and the villeins.
Held by: Derbyshire Record Office
Date: 1429
Ref; D231M/E477
There are other documents about property in the Okeover collection which name de la Pole.
(I scrolled through the de la Pole entries in NA catalogue for that century, ignoring any which mentioned Duke or Duchess of Suffolk or Earl or Countess of Lincoln.)

[Maiden Stone]

I would be looking at wills to sort out for certain the various John's in that genealogy.

Definitely. Essential.
Peter de la Pole, one of the M.P.s was a lawyer, son of one of the most successful lawyers 'in the north'. John de la Pole later M.P. sued his mother and stepfather when he came of age. The de la Pole M.P.s and friend Okeover had wardships of several orphans. They knew their way about the law.

[Guy Etchells]

If you do a search for "John de la Pole" at the Internet Archive, you'll get some interesting results. Perhaps you might find a book or two with information that will help you prove or disprove your line.

https://archive.org/index.php

Try Delapole as surname. Most will be about John,  Duke of Suffolk and his son, John, Earl of Lincoln who was named heir to Richard III before Battle of Bosworth and who later joined a rebellion against Henry VII. Mentions of de la Poles in Visitations books for counties Derbyshire and Staffordshire are more likely to be relevant.
I used de la Pole and found loads of books about Arctic explorers. 

Be very cautious when using Visitations as a source, they are very like 16th and 17th century forms of Ancestry Trees.
Some are faithful accurate pedigrees, some contain errors and a few are flights of fancy complied to please the person concerned.

Cheers
Guy

[Mike in Cumbria]

Your earliest ancestor was a collection of organic molecules somewhere in the sea, possible in a volcanic vent. How will you recognise it when you find it?