Documenting Rozaitsky - Rosenberg connection

The Matriarch of this family, at least in the US, was Toba Chaye Rosenberg
On her Vermont Death Record, she is Tobey Rosenberg, and her father is listed as Moses Fine, born Rus.
On the 1919 VT Death Record of her son "Rosenberg Simon" her Maiden Name is Tobey Fine, born Russia
On the 1920 MA Dearh Record of her son "Meyer E Rosenberg" her Maiden Name is Toibe Fine, born Russia
On the 1924 VT Death Record of her son "Hirsche Rosenberg" her Maiden Name is Tobiah Fine, born Russia
On the 1936 VT Death Record of her son "Isaac Rosenberg" her Maiden Name is Tobiah Fine, born Russia

However
On the 1933. NY Death Record of her son "Samuel Rosenberg" her Maiden Name is Toby Rosenberg, born Russia
On the 1923 NY Death Record of her son "David Rosenberg", her Maiden Name is Tobe Rosietzky, born Russia

It seems most likely her Birth Surname was Fine or something that sounded like Fine.
I believe in Samuel's case they simply gave her last name.
I believe in David's case, someone was answering the question, 'What was her Last Name before it was Rosenberg?' rather than 'What was her maiden name?" And thus that lets us know, before they used Rosenberg as a Last Name, they used Rosietzky or something that sounded like that.

(Sons names given above as appear on Death Certificates.
The Max Bloom attached as her son may or may not be her son - in any case have not seen a copy of his Chicago Death Record.
There is no Documentation showing Herbert Bloom is a son of her and/or Jacob Rosenberg, and have seen no Death Record for him - or any other record for him except a mention on records of his son, David Walter Bloom)

In her obit, https://www.geni.com/profile/documents/6000000006947956843 is Mrs. Esther Rosenberg, survived by two sisters, Mrs. M. Saiger and Mrs. I. Rosenberg.

Esther was the widow of Harris (Hirsh) Rosenberg who was the son of Jacob and Toba (Fine) Rosenberg.

Her sister, Mrs.i Rosenberg, was Zelda / Jennie Rosenberg wife of Isaac Rosenberg who was also a son of Jacob and Toba (Fine) Rosenberg.

Jacob is Yakov Yehuda on the gravestones of both those sons Isaac and Harris. Harris is Zvi Hirsh on his Gravestone.
On 1900 Census, Harris and Esther are listed as Married 25 years Suggests married about 1875
On 1900 Census, Isaac and Zelda are listed as Married 22 years, so 3 years after Harris and Esther.

Zelda's maiden name is given as Zelda Rockowsky in the Social Security Applications and Claims Index of her son Maurice (per AncestryLibrary)
and as Gilda Ratkowsky on the VT Marriage Record of her daughter Sarah
On her Gravestone, Zelda's father is given as Yitzhak Ayzik. On her NY Death Record, her father is listed as Isaac Rakofsky.

Therefore in all likelihood, this is the marriage of Harris and Esther from JewishGen / Litvak Sig - Lithuania Marriages:
Vilkija / Kaunas / Kaunas -- 20/Oct/1872 - 30 Tishri
RAZAYTSKE / RAZAYTSKIY, Hirsh -- Father: Yakov -- Age 36
RAKOVSHKE / RAKOVSKIY, Ester -- Father: Ayzik -- Age 20
Comments: Husband was a widower.

And in all likelihood, this is the marriage of Isaac and Zelda from JewishGen / Litvak Sig - Lithuania Marriages:
Vilkija / Kaunas / Kaunas -- 29/Sep/1875 - 12 Tishri
RAZANSKI, Yitschak -- Father: Yakov Yehuda -- Age 22
RAKOVSHKI / RAKOVSKIY, Zelde -- Father: Ayzik -- Age 21

Checking for when others were seeing the relationship / it was first entered on Geni

It looks like
Meyer (Rozaitsky) Rosenberg
Zarach (Rozaitsky) Rosenberg
Hirsh (Rozaitsky) Rosenberg
Khassa Rozaitsky
were each added by Dinah Berch on Dec 16, 2012 .Dinah Ronit Berch
(and she also added Max Bloom (Rosenberg) then)

It was apparently not part of the import done by Ryan Shell in 2009.