Sorry, I can't answer re the Drakelys but I do have another couple of scraps re the Uptons in Desford.
From the Desford PR (all burials):
Rebecca Upton Jun 28 1816 (which we knew), wife of John Upton Jnr
-- I'm 95% certain that it says "jnr". Now I can't see any John Uptons who were alive and who were the son of another John Upton. So maybe that simply refers to the fact that there were 2 men of the same surname in the village and she was married to the younger of them.
This date of death does rule out her widower marrying any of the other candidates except Ann Fradsham.
buried 30 Jan 1825, John Upton, FWK age 65
- this would tie in with John b 1760, youngest son of the centenarian John
Jane Upton, widdow age 73 - June 7, 1833 - this was presumably Jane nee Flabel who I think married the above mentioned John
Mary, wife of John Upton, shopkeeper, age 59 -- Dec 22 1839 -- my money would be on this being Mary Jarvis; her husband John was listed as a widow in 1841, living in Ravenstone; his offspring were bakers, grocers, maltsters, which would fit with "shopkeeper".
Not sure if this gets us much further though!