The Last Time (TLT) a living President of the United States handed the keys to the White House to a new President of the United States was in 2009.
TLT a 2 term president followed a 2 term president who himself followed a 2 term president was 2009. This is "3 deep".
TLT, before this time, we went "3 deep" was in the 1800s, with Thomas Jefferson, James Madison, and James Monroe. We've never been 4 deep.
TLT a Democrat was succeeded in the White House by a Democrat was in 1963 when Kennedy died.
TLT a living Democrat handed the keys to the White House to another Democrat was 1857. The only other time this happened was in 1837.
TLT 3 consecutive president terms were held by Democrats ended in 1953. The only time there were 4 or more was during WW2.
TLT someone became president without holding elected office elsewhere was 1953, with Eisenhower, who had been a General
TLT someone did the above but also was not a General was 1929, with Hoover, who had been in Cabinet.
TLT someone did the above, but did not hold a 'government position' (IE Cabinet, or General) was never.
TLT a woman became president was never.
TLT both major candidates were from the same state was in 1944. That state was New York.
TLT both VP candidates were governors was 1968
TLT there was a Donald, or a Hillary, or a Mike/Michael, or a Tim/Timothy as either President or Vice President, was never.
TLT a President regularly wore a wig was 1825, when Monroe stepped out of office stepped out of office.