Near as I can figure it, through the possibly flawed perceptual filters of my own reality tunnel, the most likely answers this week, seem to me to be:
Q1. Wapping
Q2. Sir Hugh Willoughby
The puzzle author appears to be revisiting old haunts with this weeks writing. The initial clues seem to place us in Wapping, in London's east end. A sixteenth century antiquary who referred to the main drag there as "a filthy straight passage", is most likely John Stow. The "well travelled writer" born c 1709, who wrote that Wapping had "such modes of life as few could imagine", is probably Samuel Johnson and the quote "awful east, helpless, hopeless" seems to originate from a book called 'The People of the Abyss', by the American writer, Jack London.
A privateer who was hanged at 'Execution Dock' in Wapping c May 23rd 1701, appears to be captain William Kidd and Judge George Jeffreys (born c 1645) was lifted by the bizzies in Wapping, as he tried to flee to Hamburg on a collier vessel. The island referred to in the text is probably Jacob's island, which was a notorious rookery, where Bill Sikes (one of the villains in Dicken's Oliver Twist (published c 1838)), met his demise, in the mud of Folly ditch, after killing his girlfriend Nancy.
A mariner who set forth from Wapping c 1553, in an attempt to find a north eastern passage to India and who probably froze to death in Russia, was Sir Hugh Willoughby (died c1554?). I did find some references to a commerative plaque in his honour, in Shadwell/Wapping. The pub called the Devil's Tavern, is now called 'The Prospect of Whitby' and seems to have had many famous customers who stopped there for a jar or two, amongst them a diarist who wrote his first entry c 1st January 1660, one Samuel Pepys.
N.B. The Eastender has moved to moderated comments due to the number of people who normally write letters in green ink, posting on his page. Rest assured though, if you have a non abusive comment relating to solving the puzzle and possible solutions, he will publish it
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