So, let's see. I tried to compile your map.
**** leaked ****
Entity func_brush (1260.00 -2439.00 66.50) leaked!
FindPortalSide: Couldn't find a good match for which brush to assign to a portal near (6412.0 2048.0 1464.0)
Leaf 0 contents: CONTENTS_SOLID
Leaf 1 contents:
viscontents (node 0 contents ^ node 1 contents): CONTENTS_SOLID
This means that none of the brushes in leaf 0 or 1 that touches the portal has CONTENTS_SOLID
Check for a huge brush enclosing the coordinates above that has contents CONTENTS_SOLID
Candidate brush IDs:
Well, this is the obvious one. You have a leak. I guess you know.
NODRAW on terrain surface!
You're not allowed to put nodraw textures on displacements. You also should really only mark the sides of the brush you want to turn into displacements before creating entities. Select the nodraw displacement faces and destroy them over the displacement menu.
Found a displacement edge abutting multiple other edges.
You have more than 2 displacments that share two edges. Basically, there are two displacements on top of each other. This may cause lighting errors, but shouldn't be the cause for your problem.
Error! prop_static using model "models/props_c17/chair_office01a.mdl", which must be used on a dynamic entity (i.e. prop_physics). Deleted.
Error loading studio model "models/props_c17/chair_office01a.mdl"!
The model you're using here can't be a prop_static, it has to be a prop_dynamic.
I'd also advise against using HL2 props for TF, because they don't fit the art style.