Post 3H Idea no. 2 (no.6 if you include the updated Xeno chart):
Lora (XC2: TTGC) vs Ashe (FE3H):
Both start out their lives seen as 'thieves' of varying consequence, Lora having awakened Jin after Gort nicked it from Torna (for this reason, it's implied that Lora didn't heist the castle, but because of her situation, correcting people was more faff than its worth), and Ashe being adopted by Lord Lonato after he caught Ashe raiding his manor, but had heard of his family's situation due to lack of a Crest (Lora is also considered 'broke', hence improvisation with Jin).
For this reason, both are seen as retainers for royalty of some description. Lora being knighted as an official Tornan Driver, and Ashe not just being Lonato's foster son, but also joining the Blue Lions at Garreg Mach Monastery.
SIDE NOTE: Both of the people who 'raised' both of these characters also end up going against either them or the people who raised them (Lord Lonato ends up going after the Church of Seiros early into the game, and Gort wants Lora dead because... well, the guy is kind of an asshole)
Both can end up 'dead' depending on the timeline. Lora's passing is questionable because Jin ends up a Flesh Eater, 'preserving' her, and versions of Ashe not recruited on non Azure Moon routes are either spared or outright killed.
EDIT: **** CSS Forum formatting w/ bullet points I DIDN'T ASK YOU TO GO HALF AND HALF.