Been offline today and see you've been busy!
You're certainly right about having unearthed a ton of info, mostly by you, so thanks as it's much appreciated. I have sent the link to this thread to my DNA connection in the USA hoping he'll talk to his family and it might trigger some recollections/family anecdotes.
Also a good point about pursuing the various Brown connections - milliners and Kathleen Browne.
Yep, still a lot of stones to turn over. Need another wet day!
I've just put together a timeline that I think has most points - might be some errors as I copied info though:
Ivy Isabel Caldwell
1909 Oct - earliest sighting - in the school records as acting in a play.
1910 Aug newspaper reports her 'indefinite stay at the home of Miss Florence McDowell'
1911 finished school with a scholarship honours - it was a 2-year course in prep for uni, but she didn't appear to go to uni.
1911-13 various mentions in social columns - visiting Miss Ruth Earhart in Chrisham and Miss Ann Grimes of Crawfordsville
1913 Chicago city directory shows mother Janet J (Brown and Connor) Caldwell - 15 E Washington - they are listed as milliners
Street Address h 413 Wrightwood av, Chicago, Illinois, USA
1914 Apr 25 Ivy married Robert Goodman (in Chicago, Cook, Illinois) so became naturalized on marriage to a US citizen.
1920 census claims born March 1891 and immigrated 1893 but we know dates aren't necessarily correct
1930 USA census shows Ivy C Goodman, 39, immigration 1893 re-stated, and Robert G, 58, born in USA, employer, lumber company, family living on a farm. States both their ages at first marriage 24. [married 1914 so born 1881]. [He had previously married Pernetta Schmid and had a daughter]. Also Owen F, 14 and Robert, 11.
1930 Oct 8 divorced. Robert jnr to live with mother. John (presumably Owen F) to live with father.
1933 Jun 23 married Raymond J Plunkett in Cook, Illinois.
1940 census with Raymond J Plunkett, and his stepsons Oliver [sic] and Robert B J Goodman
1964 Nov 17 Raymond Plunkett dies
1996 Dec 14 Ivy Caldwell Plunkett died in California.
___________
Jane Isabell Caldwell (nee Brown)
1913 Chicago city directory shows Janet J (Brown and Connor) Caldwell - 15 E Washington - they are listed as milliners. Street Address h 413 Wrightwood av, Chicago, Illinois, USA
1916 Apr 1 marries dentist James Edward Weirick (Jane born 1872 England. Aged 44 years.)
1930 Aug from Tilbury to USA last address in UK 199 Piccadilly, London. age 58. Line above shows Albert Stedman same last address, buyer, age 42 - is this millinery business? Or just coincidence as probably a common address for people about to embark?
1930 Aug arrival NY from London, USA naturalised by marriage 1916, US address St Paul, Minnesota. Age 58
1932 Aug arrival Soton of James Weirick 70 retired dentist not accompanied by wife, going to Hampton Longe [sic], Monkshorton, Ashford, Kent. This is W A Wayland's address. Further down the page there is Ganet, 61, accompanied by husband, going to London. Is this Janet?
1936 May Liverpool to USA Last UK address was Woodlands Cottage, Farthing Common, Lyminge age 60
1938 Oct arrival NY from England. US address Forect (sic) Park, Wausau, Wisconsin age 69
Newspaper report with Ivy Plunkett holding a tea at her home (Ivy's) as Janet spending winter there
[1944 June - Betsey Wayland (nee Wynn) died at Hempton Lodge, Monkhorton, buried in Lewisham]
[1944 Aug - W A Wayland widower married Kathleen Browne (In the 1932 electoral register for his London address, Kathleen was listed as Kathleen Wayland)]
1946 Dec (didn't actually embark) Spton to USA. widow Living at Woodland Cottage
1946 Dec (didn't travel though) NY from Spton widow address Tall Trees, Box 265, Wausau, Wisc age 76
1947 June arrival NY from Soton. widow. Born Liverpool. Visa issued May 5 1947. Country of residence England. Cousin Sir WA Wayland, Monkhorton, Kent. To stay with daughter Mrs Plunkett. age 77
[1950 W A Wayland died]
1960 Mar 23 died after 2 years in hospital