1. Usually from the outside. (Reminds me of a note a former colleague put on his drawings years ago - "Please note all internal glazing is viewed from the outside"
)
2. Use the Rotate command (CMD-E / CTRL-E is the default shortcut) to change the orientation (indside / outside) then mirror if necessary (if not symmetrical). Mirror-ing may well stuff up schedule elevations, so for any asymmetrical windows it may pay to ensure opening panes are placed correctly, and door / window is not mirrored. Use the "Text to indicate Mirrored doors and windows" field (usually with an * ) in the DW marker to indicate the ones you need to fix.
I think when you are placing Cadimage doors and windows now you are supposed to select the outside face of the wall initially, then direction of placement. I've still not gone as far as a window schedule with 18 yet, so I'm not entirely sure what the implications are further down the track.
Hope this helps.
(3000, yay)