I might run into you Patty, depending on your choice of time! (Holodecks linking with concurrent timelines - that's neat idea.)
My own program of choice would be to be one of the Dunedain (the boys would just have to learn to deal with a girl Ranger) patrolling the western edge of the Shire near Rivendell. (Yeah, I know - and everyone thought I was going to just say 'Thorin's Bedroom'.) I always pictured my Holodeck time in the era between TH and LOTR...but *perhaps* my goal has shifted to TH time. And if I ran into a certain exiled Dwarf that might be a very fun bit of programming...