First, I want to thank you all, as this has provided me with a lot of useful information.
Henry Allen/Allin and Elizabeth Stimpson/Stimson are my 6th great grandparents
1. Janet is the daughter of Freda Elizabeth (Pilcher) Gunn
2. Freda is the daughter of Wilda Emily (Brown) Pilcher
3. Wilda is the daughter of Fred Brown
4. Fred is the son of Hannah (Naylor) Welsh
5. Hannah is the daughter of Hannah (Woodward) Nailor
6. Hannah is the daughter of Mary (Allin) Woodward
7. Mary is the daughter of William Allin
8. William is the son of Henry Allin
Second, I have a source for some additional information
http://www.uppinghamhistory.org.uk/copyholders/copyholderspt-1d.pdf is the
Index of Copyholders Part One The Manor of Preston with Uppingham . (There is a lot of other useful information on the UppinghamHistory site)
On pg 37 and 38 it has
Henry Allin held copyhold property in Uppingham:
(a) Butlers Cottage; 14 Orange St
(b) Cottage or barn called Hillams Cottage; and Bear Yard
(c) Bear Yard lying on N side of Butlers Cottage.
In 1744, on his marriage to Elizabeth Stimson, he transferred the ownership of the property to himself and his wife.
In 1767, presumably on his death, his son and heir, another Henry Allin/Allen, and his wife, another Elizabeth, took possession of these properties.
In 1790, this younger Henry died intestate, and the properties passed to his surviving wife, Elizabeth, and his only son, William
In 1822, this Elizabeth Allen died.
This indicates that the Henry Allin married to Elizabeth Stimson in 1744 is the same Henry Allin that died in 1767.
If there WAS another marriage, to Bridgett, after Elizabeth died, she was not added to the copyhold.
According to the parish records on Find My Past, there was an Elizabeth Stimson (daughter of John and Susannah) born in Oakham in 1722 (and an earlier Elizabeth born to the same parents in 1720. I can't find her burial, but I presume she died before 1722).
Why she was in Ufford in 1744 remains a mystery (I can find no plausible Elizabeth Stim(p)son born anywhere near Ufford)