I wrote a book about the reasons for the signing of the Second Charter and 
the adventures of those who came in 1609, focusing on the experience of the 
100 women and children. My book details their struggles through the Starving 
time and into 1611. I picked apart the documents, outlining them month by 
month and sometimes day by day if that detail was available. 

I was searching my brain for the name "Sprye" and it's not jumping out at me. 
It doesn't mean he wasn't here. Of the hundred women and children, only a 
few names survived, for example.

I also brainstormed alternate spellings, which went heavily to sound. "Meese" 
for "Mays," "Pyers" for "Peirce." 

Sprye would not have died in Bermuda. One man was executed and John 
Rolfe's daughter was born and died. Otherwise, all survived.

A few thoughts:  he was probably a Captain just returning from Lowlands 
duty. Holland had just signed a truce with Spain in April 1609, and the Virginia 
Company sweetened the pot for those returning mercenary soldiers, many of 
whom brought their wives and children to Virginia. (Approximately 400 men 
came, 100 women and children.) This was because all settlers (women and 
girls included) ages 10 and up who came received joint stock rights when 
profits were divided in the future. As you mentioned, it's impossible to know 
whether he ventured his purse only without more to go on, but many of those 
soldiers did actually come.

You mentioned that the later Sprye was aligned with a Bennett. The Bennetts 
come from Wiveliscombe, Somerset. Wiveliscombe has good parish records 
online:

http://www.pbenyon1.plus.com/H_m_w/Wiv/Index.html#top

You might look for the Spryes there, including Oliver. Lots of clues buried in 
those parish records. It's highly likely the two Spryes were related.

Good luck. It's frustrating, I know!

Connie Lapallo
Author of Dark Enough to See the Stars in a Jamestown Sky
www.ConnieLapallo.com