1) For information on the original Christopher see my response to a query by Al Myers (#157 on this site). Also see NEHGR Vol. 69 p. 91 for info on Sarah Picke Strout's second marriage.
2) Marblehead Vital Records show: Sarah Pick/Pike/Picke was married to Christopher Strout at Marblehead, Ma. on Dec. 2 1680. A GeorgePicke was married there in 1684, [likely her brother]. I have notes showing that a George Pike was at Marblehead in 1668, this could be her father. I believe the source for this was either Savage or Pope.
3) Christopher # 2 was almost certainly born at Truro / Provincetown From Robert Taylor's book: "Christopher, son of Christopher Strout b. ~ 1694, buried at Mount Pleasant Cemetary, South Portland."
4) The July 1854 issue of NEHGR has a listing of Provincetown births, which includes: "Christopher, b. 26 June 1720, son of Christopher Strout and wife Mary " This would refer to Mary Hatch. I have not spent much time on this Hatch family, but she very likely descends from Thomas Hatch who was an early settler on Cape Cod. Be careful not to confuse him with The Thomas Hatch that settled in Scituate.
5) As for the Small/Smally/Smalley family: From "Old Kittery" & GDMNH & Ames Ancestry, Europe to Maine Edward Small came to the Piscataqua from St. Mary's parish, Bideford, Devon about the year 1632. He served on both the grand jury and trial jury at Saco in 1640. He had a house and land at Sturgeon Creek by 1643. He was referred to as "Mr. Small" and was a magistrate in 1645. He sold his land at Sturgeon Creek to Antipas Maverick in 1647 and was by 1653 at the Isles of Shoals where he held a license to operate a tavern. From this point forward, there is no further record of Edward Small. His wife Elizabeth (possibly Shurt), apparently never came to America. She was buried at St. Mary's, Bideford on 10 Feb. 1665.
Francis Small was baptized at St. Mary's Parish, Bideford, Devonshire on 6 Oct.1625. He came to Maine with his father around the year 1632. The first known record of him in this country is when he was taxed at Dover in 1648. He married Elizabeth (perhaps Leighton), about the year 1653.
"Little Frank [Francis] Small"b. 1671 was at Truro by 1702 [due to Indian raiding at the northern frontier].The Small descendants returned to Falmouth some 20+ years later. You will have to trace from here.