Hoping for some advice here. I'm working on a battlemap showing the courtyard of a keep. Along the edges are some buildings (the keep itself, a latrine) and then higher-level walking surfaces (stairs, the walls, corner towers, and a gatehouse over the entrance...not to mention the second floor of the keep itself). I originally figured the battle takes place in the courtyard so I'd just put roofs over the buildings. The client is saying that he doesn't want roofs, however, and would like to see the interior of the buildings. That's easy for the latrine, and maybe for the towers. It gets a bit more difficult for the gatehouse and the keep building (two floors).
Below is the full map, with roofs. Let's focus on the gatehouse for a bit. Roof on, no problems...except you can't see the "walkable" areas below it. Roof off, we can see the gate and the inner and outer portcullis. Problem is, you can also see 10'x5' areas on either side that would be the interior of the gatehouse itself. If I draw in the interior details of the gatehouse on those four squares then you have a visual continuity (confusing to the viewer) between the open area below and the upper interior area. If I do some sort of engineering style discontinuity indicator then you lose the feel of a realistic map. Some sort of transparency over the entry area might work but I think that'd be visually confusing as well.
With the keep building you've got two floors, with a second-floor balcony that sticks out over the courtyard. If I remove the roof and draw in the interior of the first floor then you've got that balcony just hanging there with no indication of how it's attached to anything. if I draw the second-floor interior then you're missing out on the doors and such that lead from the courtyard to the interior.
I should mention that there will also be a schematic map of the keep included in the adventure so, roofs on or off, the GM should be able to figure out what's going on well enough to run the thing. I've attached the rough mock-up of that as well. Neither the client nor I am a licensed medieval keep architect...which seems to be a big hinderance on this project. The details of the gatehouse, for instance, are a mystery to me (and, I suspect, to him). Do the portcullis raise up into the building? Are there winches or what? Is there some mechanism for opening the gate? Who can say?
So now I'm a little stuck and need a solution before I can advance this. Anybody have any thoughts about how to proceed?