Possible leads that arose in Answer 1 and 2 have been followed up and offered as a separate Answer.  
 
**Sherwin’s relation to Trinity House, London?**  
Sherwin’s letter to Flamsteed in 'letter 1015b' cited in Answer 2 was sent on   behalf of 'The Brotherhood’ of Trinity House (associated with pilotage,   lighthouses, navigation etc.). The Trinity House Records Manager, Neil Jones,   kindly checked their records and remarked via email:  
"I have scoured through the list of Younger Brethren from 1706 back to 1670, and have found no mention of Sherwin. Likewise for the list of Elder Brethren." Sherwin was presumably writing on behalf of Trinity House brotherhood in another role.   
The Records Manager notes that the London Metropolitan Archives hold a large amount of Trinity House records. The Court minutes, 1661-date (Ms 30004) was one suggested.   
I don't have ready access to them but they may provide some insight into Sherwin's activities with Trinity House and possibly his background.  

**Letters:** Five letters to or from Sherwin have been reported to date, three have transcripts online in the public domain as mentioned in Answer 1 and 2. My own attempts at transcripts of the other two letters are offered in the Appendix 1 and 2 from hi-res photoscans of the originals. Any comments on insights which the letters may reveal are welcomed.   

**Transcript of letter from Edmond Halley to Henry Sherwin dated Feb. 18 1704/5. (See Appendix 1)**   
Cited in Answer 1. Discusses edits of Halley's chapters 'Of Compound Interest and Annuities' and 'Constructing the Logarithms' in the Tables. The text suggested for the latter closely follows the text in the Tables on p.14. No address for Sherwin included nor any insights into Sherwin's background.   

**Transcript of letter from Henry Sherwin to Abraham Sharp dated Nov. 20 1705.  (See Appendix 2)**  
Cited in Answer 2. Discusses some promise of books by Sherwin to Sharp. The reason stated for Sherwin's planned trip to Jamaica on a postal 'paquet boat' from Plymouth seems ambiguous: "having an invitation to the [best busines] I could either expect or desire" - could mean commercial, scientific, personal? Uncertain whether the mention of being at God's disposal was just a turn of phrase or if suggests a theological background? (No record exists for a Henry Sherwin in the Clergy of the Church of England database online.)  
 
'Mr. Yarwell' is likely John Yarwell a noted scientific instrument maker of the time recorded as supplying lenses to Sharp. No lead on the 'Joshua Reyner' to date or 'Mr. Stanfield'. There seems to be extensive published research on the British postal packet boats, possibly to a likely named vessel and captain for a given date, but uncertain if these include records of passengers to confirm if Sherwin did travel, or if reciprocal info' on ship arrivals in Jamaica.  

**Speculation: Did Sherwin successfully travel to and arrive in Jamaica, if so, did he later return to UK or die there?**   
There is an extensive list of Jamaican wills online from 1655-1816 at 
http://www.rootsweb.ancestry.com/~jamwgw/sz.htm and one of these is to a Henry Sherwin 1708-9 (“RGO/SpTw/Liber 12, Folio 5, 1708-1709”). It is the only Sherwin listed in this wide date range perhaps suggesting it was not that common a local surname amongst either Jamaican residents or visitors of a status to leave a will. Admittedly speculative and could well be a coincidence that there’s a will for another Henry Sherwin in Jamaica a few years after the ‘Tables Sherwin’ was planning to go there.   

For it to be this Sherwin, would the Publishers / Printers have instigated the sometimes extensive Errata lists and corrections in the 1705/6, 1717 and 1726 editions/reprints before Gardiner was editing the third edition in 1742? Although comparing editions at www.archive.org and my own, Sherwin's signed July 1705 dated Dedication / Preface / Content remains unchanged to 1726 edition. Typically uncommented Errata were inserted up to that date, although one Errata entry in 1717 does have an unsigned comment, which if by Sherwin rather than Publishers would rule out the death in Jamaica. Quote below.  

1717 edition after p.69. "These Tables having been carefully Examined and the Errata Collected into this Page; if therefore the Reader pleased to amend the Faults in the Tables with his pleasure we presume we may recommend them to the World as the most perfect Tables this Kind now Extant."  

If the will was checked, there's no guarantee it has contents that could confirm or rule out the 'Tables Sherwin'. A death record if available may also be worth checking. It likely needs a local researcher to explore potential Jamaica leads as to date the Jamaican Records Office have not replied to query if can order copies of records. 

David Walker

**Appendix 1**
Letter from Edmond Halley, Oxford to Henry Sherwin dated Feb. 18 1704/5

*Transcript from library supplied scan with original spelling, puctuation. Text in square brackets uncertain. Halley's underlining to indicate italics in Sherwin's Tables. Final text in curled brackets was written along left edge of single first sheet, not clear what order to be read.* 
 
The Macclesfield Collection. Papers of John Flamsteed.  
Letter from Edmond Halley to Henry Sherwin  
Dated Feb. 18 1704/5  
Classmark: MS Add.9597/13/6/88 
Location: Cambridge University Library  

Oxon Feb 18o 1704[/5]  

Sr  
I received yours and will take care to give you  
your papers about annuitys as they ought to be.  
In the case you proposed tis plain otherwise than  
I took it, for by forbearance I meant that the   
annuity had been obtained after due, which you sup=  
posed, as to the last year, but then due. Which occasions  
all the disputes between us. If that be the question  
tis rather more easy than the other and I believe   
your rules are right. And if I have given trouble  
by mistaking you, I will make you amends by the  
resolutions of the two affected cases, you want.   
In the meantime that your proofs may go on, pleased  
to insert in your pag. 14 L.29 instead of the beginning of the   
break. This being laid down, it is obvious that insert   
"these words". But if instead of supposing the Logarithms  
"composed of a number of equall ratiunculae proportionall  
"to each ratio, [n]or shall take the ratio of Unity to  
"any number to consist always of the same infinite  
"number of ratiunculae, their magnitudes in this case  
"will be as their number in the former. Wherefore if  
"between Unity and any number proposed &C this I believe  
 will make it more clear. I shall be in town about [yc]   
beginning of march which I suppose may time enough  
 {for your Interest paper.  

Either
pray leave out my Captainship   
in your title.  
I am Sr   
Your humble Servt.   
E. Halley}  

Or  
I am Sr pray leave out my Captainship   
in your title.  
Your humble Servt.   
E. Halley}  

**Appendix 2**  
Letter from Henry Sherwin to Abraham Sharp Dated Nov. 20 1705  

*Transcript from library supplied scan with original spelling, puctuation and crossings out. Text in square brackets uncertain.*  

Papers of John Flamsteed  
Letter from Henry Sherwin to Abraham Sharp  
Dated Nov. 20 1705  
Classmark: RGO 1/69/C f.111rv  
Location: Cambridge University Library  

Mr. Abr. Sharp                                       London Nov. 20. 1705  

Sr. I have now before me your obleidging letter  
dated Sept. 18 which I had answerd sooner  
but that I was in dayly expectation to  
have sent you some books  but as I am  
disappointed so I cant helpe you for I [asure]  
you I never had but 6 books and I have  
given 4 of them away I could tell a long  
storie of it but I forbear onely the  
Bookseller being poor he has [pawnd] them   
all, this is the Case I have [perswaded] him  
However [I a] present you with two of them  
which I indever shall goe from hence   
by ye Carrier to Mr. [Stanfeild] next [Fryday]  
I will not promise because he seldome keeps  
his word, I will indever to be the bearer of them  
myselfe.  

It's time I invited a Correspondence with me  
at London and where ever I am in my freindship  
shall be the same but since then it has pleased  
God (at whose disposall I am) to make it expedient  
for me to live some time at Jemeica having   
the an invitation to the [best busines] I could  
either expect or desire where if I can anyway 
 
*Transcript note: letter continued overleaf* 
 
for I must be their to goe away in the Paquet  
boate that carries the letters from London the  
last thursday in this months (for their is paquet  
goes from Plimo to the west indies [the last  -  
?] after the arrivall there of the [last]  
Let Thursdays letters from London every  
month) and I must set out from London on  
Wednesday 28 inst in the morning, I take  
my leave at present wishing that hereafter  
I may be servicable unto you, in the least  
matters, and can never but value my selfe  
upon yr freindship. Mr. Joshua Reyner lives  
at Long Houghton near Wakefeild Yorkshire  
upon the Receipt of your letter I went to Mr.   
Yarwell who said he did not know what was  
wanting in your last parcell but if you  
would write what would be most acceptable  
he would send it you, if you write to me  
to be in London on Monday next pray  
write a letter to him at the bottom I will  
deliver it him pray excuse my hast and  
give me leave to subscribe my selfe  

Sr. your obleidgd freind  
and humble Servt  
Hen. Sherwin