This is the perfect place to ask your questions and get some help on WikiTree.
If this seems to be your family line below, you might try the free search tool at: https://familysearch.org/search to see if you can find more records. If you know the names of any of your grandfathers siblings, you might find him in the 1930 census, with siblings and parents listed. Then you can plug in the names/dates/locations to find additional information. The public census data only goes to 1940 – so you wouldn’t find your dad and forward on census data. Same for Carrie Holt (Dillon).
Larry S Harless Find A Grave Memorial# 136328058
Born Wednesday, March 3, 1948 in Oak Ridge, Tennessee, he was the son of the late Charles Harless and the late Carrie (Holt) Dillon.
United States Social Security Death Index
Citing this Record: "United States Social Security Death Index," index, FamilySearch (https://familysearch.org/pal:/MM9.1.1/JYKP-BXS), C E Harless, 04 Aug 1992; citing U.S. Social Security Administration, Death Master File, database (Alexandria, Virginia: National Technical Information Service, ongoing).
Given Name: C
Middle Name: E
Birth Date: 9 December 1924
Social Security Number: 408-24-9940
Last Place of Residence: Livingston, Kentucky
Previous Residence Postal Code: 42081
Event Date: 4 August 1992
United States Public Records
Citing this Record: "United States Public Records, 1970-2009," database, FamilySearch (https://familysearch.org/pal:/MM9.1.1/K5JK-HD5 ), Charles Emmitt Harless, Residence, Smithland, Kentucky, United States; a third party aggregator of publicly available information.
Name: Charles Emmitt Harless
Residence Date: 13 Nov 2000
Residence Place: Smithland, Kentucky, United States
Birth Date: Dec 1924
Phone Number: 554-3566
Phone Number Recorded Date: 13 Nov 2000
Address: 1 RR 1 17
Address Continued: Smithland, Kentucky 42081
Address Date: 13 Nov 2000
2nd Address: 4504 At Massa Dr
2nd Address Continued: Paducah, Kentucky 42003
2nd Address Date: 01 Aug 1994-01 Jun 1996
3rd Address: 1924 Kentucky Ave
3rd Address Continued: Paducah, Kentucky 42003
3rd Address Date: 01 Aug 1968-11 Nov 1997
Possible Relatives: Janette Harless, Jeanette E Harless, Mary J Harless
Record Number: 96702276