hmmm, I've actually given question #1 some thought before and think I would choose Bela Fleck's excellent instrumental "Sanctuary" for my funeral. The version from his "Drive" CD is my favorite, with Sam Bush, Tony Rice, Stuart Duncan and Jerry Douglas among others.  It starts out slowly and seriously with a sort of sad undercurrent at first, but as it moves along it begins to pick up steam and tempo until finally, it lifts you up in a powerful, but also joyful kind of way.  Great song. Like you too, I would want them them to play something a little more playful too and believe I would choose "Spirit In The Sky" by Norman Greenbaum for that one.

As for a song that makes me think of my mom...I guess that would be "Up, Up and Away" (as in...my beautiful balloon) by Jimmy Webb and sung by The Fifth Dimension.  I remember when it was a hit back in the late 60's and we took a flight to California where they were playing it on the in flight music channel. I will always remember the big smile on my mom's face that day as she anticipated a relaxing vacation, with her eyes closed, the headphones on ...just wearing a very pleasant aura in general.