G'day Tankluver. You don't seem to have drawn too many replies but i am sure you will get some soon...lol. I by no means consider myself a diorama expert but i will try and see if i can help.
As to using a wooden base, well that is fine but just make sure you seal it first. In one of my first diorama attempts i purchased a wooden cutting board which had nice edges and was just the right size for what i wanted. The mistake i made was to put down a layer of plaster straight onto the board. I textured the plaster(i thought)really well and added some grass and was quite pleased with myself only to have the whole thing warp on me not long after. So i now coat any wood with some type of varnish. You sure learn by your mistakes.!!
Not quite sure what you have in mind by 'drilling an outline' but if wanted to secure a building to your base you could drill holes in the base that line up with holes in the building and use some sort of pins, maybe small diameter wooden dowel or even pieces of sprue. Also , if you build up the surrounding groundwork against the base of the building that should hold it too.
What you make your building out of will depend on what type of building you want to portray. Both mediums you mention can be used effectively. There are some nice kits of buildings on the market. Have a look at a diorama forum post done not long ago by marevic1. He made a really nice building, i think out of plaster, and i am sure he described how he did it too. It turned out really great
Check out Shep Paines book 'How to Build Dioramas',(gets mentioned a lot on here) and also 'How to Build Armor Dioramas' by Lyn Kessler. I have both and that are fantastic references.
Hope you get the answers your looking for. Happy modelling...
Boomer..