I love playing Halflings. For the moment, I have never played with modes so I just played Thiefs, F/T and Clerics. I have to say that for me the quintessential Halfling is a simple vanilla Thief, a role which fits how I see Halfling (of course influence of LoTR) and how I imagine Gorion's ward.
At the moment, I am running a character called Lily Weatherbee, vanilla Thief. Usually, my characters have a maximal strength of 8, which fits I think Halfling's size - and weight allowance. I try to be "realistic" regarding to objects - Lily can only wear armor custom-made and not armor found in the field. Zhurlong's boot are OK (he is too a Halfling). Her weapons are dagger and sling - perhaps latter she will learn to use darts.
I have an other Halfling character, Myrtle Leafshadow, a Priest of Lathander. I love her, but it is still strange for me to play a non thief Halfling (pity she cannot be cleric-thief like a gnome).
What are your experiences with Halfling characters ? I would be interested to hear and surely learn from them. Have someone run the whole trilogy with an Halfling character ?