1. Nope, nowhere near you. I'm hundreds of miles away, sitting at my computer with Ancestry.com, a bowl of popcorn, and a beverage of choice. I'm a volunteer with time on my hands, a liking for genealogical puzzles, and sometimes a little luck. I like to do "Interesting Work for Nice People". I suspect that I'm much like many of the people who respond to these queries.
2. You might consider posting queries on the Mississippi general and Lee County forums, both here and on GenForum. Many of the people with Mississippi interests may not follow this United States general forum, and so would miss the opportunity to help you further.
3. For free Social Security Death Index info, try:http://search.ancestry.com/search/db.aspx?dbid=3693
There's also a slightly different version on RootsWeb.
Given your grandparents' ages, however, they probably won't appear in the index. They may never have participated in Social Security. Some of your later relatives should appear, though.
4. The four 1917/1918 World War I Draft Registrations covered men in the United States who were born 09/13/1872 - 09/12/1900. This got 98% of the men in the country--exempting only men alread serving in the military. Aliens, too, had to register but not serve.
Having said that, here's the detailed info on your grandfather (from Ancestry.com, of course!):
09/12/1918 Registration - Tupelo, Lee County, Mississippi
Simon Richard BOYD of RFD#1, Tupelo
34, white, native-born on 06/30/1884
Farming - with wife Lila (Rachel?) BOYD, same address
He "made his mark", or did not (could not?) sign his form.
He was 5-3/4 feet tall, with medium build; and had blue eyes, dark hair, and no listed disabilities.
If he had brothers, cousins, etc., that fell in the same age bracket listed above, they should similarly appear. Same thing for Lila's kin.
5. Now, a year-and-a-half later, we see this even more detailed information on Simon and his large family in the 1920 Federal Census for Mississippi - Lee County - Verona (which may be the same as RFD#1 Tupelo). The information is "as of 01/01/1920". The image is a little faint, but I think that this is fairly accurate:
Simon R. - Head, 35
Linda R. - Wife, 30
Ella M. - Daughter, 12
Ada L. - Daughter, 10
Oscar (T.?) - Son, 8
Annie B. - Daughter, 7
Georgia O. - Daughter, 2-11/12
Clara E. - Daughter, 6/12
with them in the same household are:
Sarah - Mother-in-Law, 69
James S. - Brother-in-Law, 27
This is a white farming family. Simon and Linda (Lila?) are married; Sarah is widowed; James and all the other childen are single.
Everybody and their parents were born in Mississippi - EXCEPT
Sarah's father was born in South Carolina, and her mother in Scotland!
Did you see your parent in the list?
Look at the children's ages: Ella was born about 1907, so she and her parents should be in the 1910 census. Georgia and Clara, born about 1917 and 1919, should still be at home with parents in the 1930 census.
You should be able to do similar work with the TODD/HOLCOMB folks.
6. And last: did I mention RAOGK (Random Acts of Genealogical Kindness)? Try www.raogk.org
to see if there are volunteers in Mississippi, perhaps specifically in Lee County, who could help you with local research.
Good luck - and continue to have fun!