I might be missing something silly, but is there a way to guarantee that each point label in my point layer gets displayed?
Use (without maplex)
Label Priority, Label Weight Ranking & Place Overlapping Labels http://help.arcgis.com/en/arcgisdesktop/10.0/help/index.html#/Setting_label_weights_and_feature_weights/00s80000001p000000/
(with maplex) http://help.arcgis.com/en/arcgisdesktop/10.0/help/index.html#/Reducing_the_size_of_the_label_text/003s00000035000000/ reduces the size of the text to fit all to the map.
Alternative > convert text to annotation at different sizes.
in 9.3 there is a check box for place overlapping labels. this still will not absolutely positively always label your object. with the maplex extension it does work more often than not. The next best(worst) thing is to select your layer with labels turned on and convert labels to annotation. then you have to edit the annotation and show unplaced annotation. changing it's status to placed and moving the text to where you want it. the long way around to something that seems so primarily needed. Btw to help you with shortcuts... the long way around produces a much cleaner, nicer looking map than does place overlapping. It can get really ugly depending on the scale and frequency of the labels.