Long story short I was given a box of old records and photos and a Masonic sword by my last surviving uncle on my fathers side. I'm the last male in the tree 
So I decided to do some research as my Uncle couldn't figure out who "Wade" was (name inscribed on said sword). Turned out I was able to positively ID "Uncle Wade" my Great Great Uncle from my grandmothers side of the family. The Sword is apparently from somewhere between 1880 and 1910
Down the rabbit hole I went. Now I'm knee deep in Ancestry.com and FamilySearch.org and tracking all 4 branches of my family.
I'm back to the 1600's on my Fathers side and the 1500's on Mom's side.
Once you get your grandparents and possibly some Great Grandparents info in there, the system is pretty good about matching records and taking you back further.
A couple of things I've learned
As with most complex problems, Bourbon helps

So I decided to do some research as my Uncle couldn't figure out who "Wade" was (name inscribed on said sword). Turned out I was able to positively ID "Uncle Wade" my Great Great Uncle from my grandmothers side of the family. The Sword is apparently from somewhere between 1880 and 1910
Down the rabbit hole I went. Now I'm knee deep in Ancestry.com and FamilySearch.org and tracking all 4 branches of my family.
I'm back to the 1600's on my Fathers side and the 1500's on Mom's side.
Once you get your grandparents and possibly some Great Grandparents info in there, the system is pretty good about matching records and taking you back further.
A couple of things I've learned
- Once you get back to the early 1800's and late 1700's, written records become few and far between
- They didnt have spellcheck back then (who knew) and names, even last names, can change on records depending on who wrote it down, and sometimes its written correctly but transcribed wrong
- You have to match documents to be sure you're following the right person. Census, marriage/Birth/Death certificates etc. Hell of a lot of duplicates with slight misspellings. It can get very messy very quickly. Dont jump to conclusions
- Thank God my last name isnt Smith
- You can track down in many cases who came over on the boat,and which boat from Europe as there are ship logs for a lot of them. (Was able to ID a direct descendant? and family to the the ship "Phoenix" arriving in 1751)
- Women who have multiple husbands and children by multiple, make a real mess out of things when you're trying to trace a name. "Grandma Jones" had 4 husbands, all with children, and another out of wedlock
- Once you get to the early 1700's/1600's church records/baptisms etc become a primary source
- Just when you think you've got it all sorted out, you find a discrepancy mid way through the tree making everything past that point WRONG!
As with most complex problems, Bourbon helps
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