As for the time line thing, I wanted to do something that showed all the years that we have been together as well (8 by the time the wedding rolls around). I was thinking of something like this:
I wanted to show off our vacation pictures from over the years because we have gone to some pretty cool places. Plus we are getting married in New Orleans and then coming home for the reception. Thought I would add some shots from the wedding in there as well.
Games sounds like a good plan to get people who might not know each other to talk. I like the idea of leaving some trivial pursuit cards on the tables. I think I lot of people have also been using kootie catchers (is that the name?). I was considering doing a couple with different themes - like using them to foretell your perfect vacation spot, would you survive the zombie war, retirement plans, etc. Not sure if that makes sense in writing, but yeah...
Crosswords are a great idea and I know you can make some with all your own words/clues - but that might not work too well at getting the conversations going at the table.