Port Chester: How did the Nolan Family decide to move to Port Chester from Manhattan?

I am a huge fan of How I Met Your Mother so the narrative of a young couple starting a family and moving out of The City to Westchester County is familiar; I set out to document my family's migration from New York to White Plains and eventually Port Chester. 

My grandmother's story explains..."After Anne and John were married they moved to White Plains to work for Whitelaw Reid, the owner of the New York Tribune and one of the most illustrious reporters of the Civil War." 

Anne and John are living in New York (East 25th Street) and worshiping at Immaculate Conception in 1868.  In 1869, their son John, drowns in Purchase New York and in 1870, their newest son (also named John) is baptized in White Plains in 1870.  These facts place the Nolan's move to Westchester as happening likely sometime between 1868-1870.

Whitelaw Reid moved to Ophir Farm, in Purchase New York, in 1887. If Anne and John moved to White Plains to work for Mr. Reid - it would mean he had a different home or presence in the area - because in 1870, Mr. Reid is found on Lexington Avenue in New York City (a bachelor.) In other words, it may be that the move to the area was for another reason.

Theories I've researched: 

Did Anne and John work for the Reid Family?

Tom and I spent the day in Washington, DC. reviewing the personal papers of the Whitelaw Reid family. The collection spans Whitelaw's life and includes papers from his wife(Elisabeth), his son (Ogden) and Ogden's wife (Helen) as well as Whitelaw's grandson (also Whitelaw).  It includes an exhaustive (and exhausting - ask Tom) set of Whitelaw's personal correspondence, in which he talks a great deal about his work - as Editor of the New York Tribune and later as Ambassador to the United Kingdom.

Correspondence from the 1890s discuss his property in Westchester County (Ophir Farm) and the fire.  Ogden's records document the farm's loss of income with their efforts to raise and sell sheep, cattle, pigs, chickens, and dairy cows. There are lists of laborers; the dates however, are after John's death, so this area of research proved a dead end.

Elisabeth's record's document her charitable donations and seem to have been pulled together to provide assistance in the preparation of income taxes. There is no mention of household help.  So no mention of Ann does not mean they did not employ her - but no evidence found is just that - no evidence found.

Jane Templeton Cunningham (Jane T.) Elisabeth's mother, kept a household book and it has entries from 1872, listing names of house maids, and one name listed is Ann. 

Jane T. and her family (father James Cunningham) lived in Westchester County; 

Jane married Darius Mills (also from Westschester County)  in Irvington in 1854.  Darius's family are described as humble farmers.  

Jane and Darius were active in Manhattan society they lived on 5th Avenue  and owned a mansion in San Mateo, California. I wondered if Darius owned a home in Westchester County.  Darius seemed to maintain a connection to the area (both he and Jane are buried there.)  I further wondered if  Ann had worked for Darius and Jane, and remained  with the family after Elisabeth married Whitelaw

... yes a stretch... 

And,  I have not found evidence of the Mill's living in Westchester.  

In other words, this Ann listed in Jane T.'s book is probably not our Ann.  

Because, remember, the dates don't really match up - the Nolan's are in Westchester by 1868 - and the Reid's arrive 20 years later. 

Did Anne and John work at Ophir Farm before Mr. Reid purchased it and then stay on after the ownership transferred? 

Anne and John's son, John, drowned on Ben Holladay's farm in Purchase New York in March of 1869. 

Ben Holladay was an American transportation businessman responsible for creating the Overland Stage to California during the height of the 1849 California Gold Rush. 

The land he owned in Purchase  became Ophir Farm. Holladay purchased 1,000 acres in 1864 and built a
mansion for his wife, Ann Calvert a deeply Catholic woman from a wealthy family (who were horrified by her choice in husband.)  Holladay built her a palace (100 rooms) in Purchase New York and named it Ophir after his mine in Nevada; Holladay won the mine in a poker game. 

In The Panic 1873 (18 September 1873)  Holladay lost his fortune in the stock market crash and Ann died (yes same day.)  Holloday lost Ophir Farm and left Westchester County for San Francisco.

Did the Nolan's in fact work for Holladay? Does this explain why John was on the land, ice skating or playing? Is the Nolan family move to Westchester (approximately 1868) done so they can work at Ophir Farm for the Holladay's? 

What next -- need to find evidence of employment

Any ideas?

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