Sorry for the delayed, my liver was still recovering from friday night.
1) you don't have to, but i like drinking my ruby's colder and then have them come up to temp as the night goes on
2) Ruby's in general are meant to be drunk young. You could age them but they'd just throw alot of chunky sediment and potentialyl turn tawnish.
3) I pair it with Sichaun food. https://thewoksoflife.com/fuqi-feipian-sichuan/
that is honestly one of the best pairings.
If you want to go more traditional route. a good salty english blue and some almonds.
if you wanted the chocolate route, make sure the chocolate is sweeter than the point. So i like milk chocolate. if you go dark chocolate, you might acutally get more greeness out of the port than expected, not to mention the bitterness in the chocolate.
I personally prefer the more savoury notes you get with the blue cheese and nuts.