I believe the problem is that ALL these entities are being jammed into
the "Building" pointer too fast.

To test this, put a "wait(1);" between each building type.

I think what is currently happening is that "court.mdl" is large,
and is still being loaded when the next ent_create gets processed.
Because court.mdl is still being loaded, then "road.mdl" CANT get loaded,
because the Building pointer is still "busy". Hence the error.

But why are you putting all the entities into the single Building pointer anyway?
The Building pointer will only store the last one you ent_create, and all the
other entities will still exist, but you will have no way of accessing them.