Well done to Colcaff for finding the marriage.
Looking at Griffiths Valuation for Drumlane in 1858, there were 2 Sims farms there. Probably father & son. William Sims junior had plot 1 which was a 44 acre farm and William senior had plots 2 & 3 which totaled 167 acres (so very big by Irish standards). Those properties today are up a lane off the modern Drumlane Rd, about 4 miles south of Kilrea. I think they may have been combined into 1 farm.
There are no Laurence properties listed in Drumoolish in Griffiths so they may have moved away from the area.
Some Probate abstracts from the PRONI wills site:
The Will of William Simms late of Drumlane County Londonderry Farmer deceased who died 2 January 1877 at same place was proved at Londonderry by the oath of John Falkiner of Craigs County Antrim Farmer one of the Executors.
The above will is on-line and mentions his wife Nancy Graham, but no children, so possibly they didn’t have any. The date of death may be incorrect. It appears on the GRONI website as 2 January 1876, aged 58.
Administration of the estate of James Simms late of Drumlane Kilrea County Londonderry Farmer who died 3 January 1897 granted at Londonderry to Jane Simms the Widow
The James listed above died intestate and his probate file was destroyed in the 1921 fire in Dublin. No papers survive other than this abstract. The date of death also seems to be incorrect with it appearing on the GRONI site as 3 January 1896, aged 54. The informant was James’ daughter Annie Simms:
https://civilrecords.irishgenealogy.ie/churchrecords/images/deaths_returns/deaths_1896/05909/4677173.pdf
Annie married James G. Kirkpatrick of Tyrgarvil on 9th April 1898.
https://civilrecords.irishgenealogy.ie/churchrecords/images/marriage_re…
1901 census. Just 1 Simms household in Drumlane. Note that the family are Reformed Presbyterians (also known as Covenanters). The nearest RP church is probably Drumbolg, so their records may be worth looking at, if you can’t find them elsewhere. Their records are held at PRONI, as follows: Baptisms, 1895-1956; marriages, 1864-1925; session book with discipline cases, 1809-59; committee minutes, 1887-1919.
http://www.census.nationalarchives.ie/pages/1901/Londonderry/Tamlaght/Drumlane/1521301/
By 1911 the family has changed to Presbyterian:
http://www.census.nationalarchives.ie/pages/1911/Londonderry/Tamlaght/Drumlane/592343/
Simms William Alexander of Drumlane Upperlands county Londonderry farmer died 29 December 1940 Probate Belfast 9 April to Thomas Lytle and Robert McIlfatrick farmers. Effects £1007 15s.
The will for the above William Simms should be in PRONI, in paper format.
Annie Kirkpatrick (nee Simms) in 1901:
http://www.census.nationalarchives.ie/pages/1901/Londonderry/Swatragh/Tergarvil/1545808/
1911:
http://www.census.nationalarchives.ie/pages/1911/Londonderry/Swatragh/Tirgarvil/611900/
By way of explanation, the surnames Kirkpatrick and Kilpatrick are interchangeable (a bit like Henry & Harry or Nancy & Agnes) and you will note they have used Kirkpatrick in the 1901 and Kilpatrick in 1911. There were many interchangeable surnames in those days. Other examples are Robertson & Robinson, Connor & Nogher, Faulkner & Falconer. Having a single “correct” spelling of your name was not a concept our ancestors would have recognised. All designed to make research a bit more challenging).