You probably will get a better reponse if you post each family separately in the county you know or think they lived in.
I picked one family and here is what I found.
A James Kester in 1900 was living in Meeteetse, Big Horn Co., WY.
James Kester, b. OR, 17, single, sheep herder, both parents born i OR.
A James C. Kester b. 18 May 1907, 16564 Dixonville Road, Roseburg, OR. Source: U. S. PUblic Records Index, Vol. 2, Ancestry. This might be James Clyde.
In 1910 the Kester family lied in Deer Creek, Douglas Co., OR.
James J. Kester, b. OR, 27, marr 5 yrs, no occupation.
Lora, b. IA, 26.
Clyde, b. OR, 2.
Hazel R., b. OR, 1.
Ethel R., b. OR, 1.
A James Johnson Kester b. 5 April 1883 in 1917 or 1918 was living in Douglas Co., OR. Source: World War I Draft Registration Cards 1917-18, National Archives, Ancestry.
In 1930 the Kester family was living in Mill, Douglas Co., OR.
James J. Kester, b. OR, 46 yrs old, general farmer, marr @ 22.
Lora M., wife, b. IA, 45, marr @ 21.
J. Clyde, b. OR, 22, single, clerk poultry house.
Hazel R., b. OR, 21, single.
Helen M., b. OR, 19, single.
Belle, b. OR, 17.
A James J. Kester died 2 Jan 1956, Douglas Co., OR. Spouse-Lora. Death Cert=196. Source: Oregon Death Index 1903-98, Ancestry.
A Lora Kester, b=27 Jan 1884, Last Residence=Roseburg, Douglas Co. died Feb. 1979, Roseburg, Douglas Co. Her soc. sec. # was assigned in Oregon before 1951. Source: Social Security Death Index, Ancestry.
A Lora Mae Kester b. 27 Jan 1884, died 6 Feb. 1979, Douglas Co. per death cert #79-02165, Spouse=James. Source: Oregon Death Index 1903-98, Ancestry.
A J. Kester b. 18 May 1907, Last Residence=Roseburg, Douglas Co. died May 1985. His soc. sec. # was assigned in Oregon before 1951. Source: Social Security Death Index, Ancestry. I think this is James Clyde Kester.
You can request copies of their obituaries from Random Acts Genealogical Kindness. Go to raogk.org/, read guidelines, choose Oregon, choose Douglas Co. and choose one volunteer.
Ask the other volunteer about marriage records for the daughters. Then you can look up their death info from the Social Security Death Index at Rootsweb.com home page. Successful Searching!