Fred
I am not sure what you are doing wrong here - so I built an example that appears to work for me at least - here is what I did - hope that these steps may help
- I built 3 surface models - Datum 100, Datum 103 and Slope Plane (Elev 95 on Left and 108 on right). All three were a square from 0,0 to 1000,1000 drawn as a rectangle and then elevated accordingly. The two Datum surfaces are flat planes at Elevation 100 and 103.
- I then drew a Dynaview Frame (a 4th rectangle from -10,-10 to 1010,1010).
- I then made surfaces for the two Datum Surfaces and the Slope plane surface
- I then created CF Maps for the Datum 100 to Slope Plane and Datum 103 to Slope Plane combinations.
- I then imported my Plot Sheet Template (I used Arch D sheet but this should not matter
- I then created View Filters for the displays I wanted - CF Map 1 and CF Map 2 - these showed the CF Map Surface, The Linework and the Cf Labels for the correct CF Map - the Labels for the two CF Maps were on different Layers.
- For steps 8&9 below I used the Mixed Sheet Sheet Set and created a Custom Sheet
- I then created a Dynaview for CF Map 1 on the custom drawing sheet - on creation I selected the View Filter CF Map 1 (You can change this through properties of the Dynaview on the Sheet layout)
- I then created a Dynaview for CF Map 2 on the same custom drawing sheet - on creation I selected the View Filter CF Map 2 ()you can change this through properties of the Dynaview on the Sheet Layout
At this point my Project looks the same as yours I think (in principal)

Now I Print Plan Set - I select the Mixed Sheet Sheet Set and the CF Maps Sheet that I created as a custom Sheet
I select Print to PDF and this is what I get in the PDF File - this is what you wanted I think - I have the All View Filter set in my Sheet View but it would have worked with CF Map 1 or 2 View Filter also as that includes all of the Sheet Layout stuff as well as the specified CF Map data. I dont think that is the issue here but it may be - make sure that each view only has one of the CF Maps in the View Filter applied to the Dynaview and make sure that ALL View Filter is applied to the Sheet View itself - it could be that both your Dynaviews are showing both CF Maps, but the display priority is winning to show only one or the other and that may also affect what comes out to the PDF Output.
I did not place the legends on mine but that is an easy addition and I am sure makes no difference here.

Hope that this answers the question
My example and the PDF Output is here if you need to take a look at it
Alan