Ullock Mains
The Woodhall property was at Ullock Mains. John Woodall (-1719) , Oswald's great-grandson, described himself in his will as 'of Ullock', but described his property as in Ullock Mains; and there is no reason to suppose that Oswald didn't live there too. A datastone at one of the farms in the hamlet (opposite a main Fearon property) has the initials 'OW' and 'EW' with the date 168?, a clear reference to his grandson Oswald Woodall (1661) and his wife Elizabeth.
The farm buildings look impressive now - and imply high status then.
From Google Streetview
Place within the Woodhall family
Oswald Woodall was probably a younger son of John Woodhall (-1553) of Ullock (and so brother of the John Woodhall of Ullock who married the sister of the future Archbishop Grindal). There is no absolute proof of that, but the dates and logic fit.
One reason for thinking this is his forename. There is no evidence for the use of the name Oswald within the Woodhalls, but there is in the Crakeplace family - and his apparent mother was a Crakeplace (the argument against is that the parish church of Dean is St Oswald, so there could be other reasons, such as illegitimacy, for the baptismal name). Furthermore, Oswald's family used the forenames Thomas and John, as did the the Woodhalls.
What amazes me is the very fast stream between northern rural gentry/yeomanry and London power.
Status
Oswald would not have shared in the Archbishop's generosity in any way - that was his brother John's good fortune, not his; but he would have been able to claim (in the terminology of the day) to be a brother-in-law of an archbishop. His Woodhall ancestors were gentlemen, if not quite gentry like the Lamplugh family; his Crakeplace ancestry was ancient; and his cousin Christopher Crakeplace was, as servant of James Altham (to be knighted at around Oswald's death), connected with London finance and with Flimby coal.
He didn't inherit a major freehold, but as a younger son he would have got a significant inheritance or been a good catch for a marriage. The farm at Ullock Mains, whether originally a Woodhall property or not, was a substantial tenement - and he a leading yeoman. Quite possibly literate himself, he would have commanded respect, the more so as he aged.
Age
Two Oswald marriages are recorded in the Dean register, in 1559 and 1579. The first would imply that Oswald was born c1524-1534, quite a bit younger than his elder brother John who married in 1542. This marriage, however, can't be his first - the second of his grandchildren (John) was baptised in 1567, so the father would have been born some 20 years earlier, a long time before the 1559 marriage. Oswald, therefore, probably married a first wife in the early 1540s, and had a birth date around 1517. He would have been around 90 by the time of his death in 1608.
The uncertainty is caused by the lack of registers in neighbouring parishes. Dean and St Bees have surviving registers - Lamplugh has a register from 1581, Loweswater and Arlecdon not at all. If Oswald's first wife came, say, from Lamplugh and gave birth to their first child, Thomas, at the maternal home, then we wouldn't have (as indeed we haven't) any surviving record of the marriage or the baptism.
Life
His unknown first wife would have been from a significant local yeoman family.
By his first wife, he had a son Thomas (alive 1594).
He married again (10-05-1559) to Margaret Payll [Peile], and they had three daughters: Elizabeth (baptised 20-08-1561, buried 01-04-1561/2), Jane (baptised 11-09-1573) and Margaret (baptised 26-02-1575). Margaret was buried 26-02-1575, the day of her daughter's baptism.
It is possible that Oswald married a third time in 1579 to Mary Salkeld. With a 4 year old daughter, that would make perfect sense, but would not be a necessity as his son Thomas was then in the midst of raising his own family on the farm (Thomas' wife would have looked after the child). It is much more likely that this marriage belongs to a younger Oswald.
He was a prizer for Christopher Pearson, miller, of Ullock in 1583. He was buried 29-12-1608.
A possible tree, giving Oswald a third wife. The option below seems more likely.
A possible tree with a son Oswald
Children
Thomas Woodall (alive 1600) of Ullock
There is nothing much to say about Thomas, other than that he had six children. No baptism date or burial date. No probate. He was probably born in the mid-1540s, was live in 1600, and probably died after the Dean register stopped in the 1620s. So he might well have lived into his 80s or 90s like his father.
His children were: Thomas, John (baptised 30-02-1567), Henry (baptised 25-10-1570), Oswald (baptised 15-06-1594), Susannah (baptised 26-02-1600, buried 26-02-1600) and Mary (baptised 26-02-1600, buried 27-02-1600). The last two were presumably twins.
Oswald Woodall (alive 1610) [of Branthwaite?]
An 'Oswald Woodhall' was prizer for Cuthbert Rogers in 1610. He may have been Oswald's son. He does not appear to have had any surviving children.
Jane Rogers (1573-)
Jane was probably the Jane Woodhall who married 21-08-1594 in Dean to John Rogers. He may be John Roger of the Browhead or John Roger of the Nook, possibly father and son, who both appear as witnesses in the will of John Fearon of the Edge in 1608. John Rogers of the Nuke [sic] died in 1619.