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Cherokee research begins with the basics of genealogical research.
You must do your homework... read genealogical how-to books and websites to learn the basics.
Do you have your pedigree chart and family group sheet completed for all four lines (paternal & maternal), documented with all or most of their children and who they married? You won't accomplish a lot if you haven't done your basic work. Sure you'll have missing information, but it is upon this information that you will base your research to find the answers.
Have you located the four families on the 1930, 1920, 1910 and 1900 census? Census records are a big help because they can help you learn where each family member was born; where the parents of each person was born; how the couple has been married; if one of the spouses was married before; how many children the mother gave birth to and how many of those children are living at the time of the census; and you'll learn the month and year of each person was born on the 1900 census. There was no US census of the citizens living in the Cherokee Nation until 1900!
By now you should know exactly where your ancestors were living in 1930, 1920, 1910, 1900, and have a list of their known children recorded on your Family Group Sheets. With this information you are now ready to begin checking the Cherokee rolls. There are NO shortcuts.
To become enrolled as a Cherokee today you must find a direct ancestor on either the Dawes Roll or the Guion Miller Roll of Eastern Cherokees. A pre-requisite for all subsequent research requires that you examine both of these rolls.
If the person you are looking for lived in the 1900's and
lived in Indian Territory, NW Arkansas or Southern Missouri you should check:
Dawes Roll for your family members
The Dawes required a residency in Indian Territory, but some living in NW Arkansas and Southern Missouri met the requirement at the time the Dawes Commission began.
lived anywhere else in the United States you should check:
Guion Miller Index to see if another the family member applied for enrollment
Guion Miller Roll was the first roll that people living anywhere in the United States might be eligible for enrollment as a Cherokee.
If the person you are looking for lived in the mid 1800's check
The Siler Roll, Chapman Roll and Act of Congress Rolls taken in states east of the Mississippi River
The Drennen Roll in Indian Territory for Cherokees who emigrated at the time of the Removal and prior to 1851
The Old Settler Roll for Cherokees who had emigrated to Indian Territory prior to the Removal
If the person you are look for lived during the 1850-1855 period and lived West of the Mississippi you should check for their names on the Old Settler Roll and Drennen Roll.
If the person you are look for lived during the 1850-1855 period and lived East of the Mississippi in the states of North Carolina, Tennessee, George, or Alabama you should check for their names on the Siler Roll and Chapman Roll.
Now you've gathered the relevant data and either found some family members on one of the rolls or not... It's time now for the next very important step. Laying out your research strategy - evaluate the evidence you've collected and plan a strategy for future research.