Yeah that's a little more diffcult, the problem you're having with Surface Area is that in order to pick multiple surfaces they have basically to be four sided and the corners where they meet have to intersect within a certain tolerance that is set under Preferences, Selection, Chaining Tolerance. So short of building a sheet or sheets that encompass all of the surfaces using Through Curve Mesh, or N-Sided Surface that meet the Chaining Tolerance, I don't think that Surface Area is going to help here.
You could maybe try a Z-Level Profile op. with the Part selected and the surfaces selected for Cut Area and the cut levels set to scallop in Common Depth per Cut but I'm not familiar with the possibility of undercutting areas with this op. but if you can get this to work make sure in the Non Cutting Moves - Trim to Min. Clearance is checked with a specified Min. Clearance in the engages and retracts or else the cutter may violate the part on these.
I'm sure there is a better way of doing this, maybe someone else can chime in with a better approach.