I think you need to review the Help System (Windows).
There are many files that deal with 'help', including the index files. A sample (acad.chw) file:
[Options]
ResultLimit=15
RankStyle=1
TabSource=ac.AwTab.htm
Language=0
EnableSubset=1
[Files]
Count=13
1="acad_aug.chm"
2="acad_acr.chm"
3="acad_agi.chm"
4="acad_dpg.chm"
5="acad_acg.chm"
6="acad_vlr.chm"
7="acad_vlg.chm"
8="acad_vlt.chm"
9="acadauto.chm"
10="acad_aag.chm"
11="acad_car.chm"
12="acad_dxf.chm"
13="acad_asa.chm"
[Subsets]
Default=2
ShowBookCode=1
Count=18
1=1,2,3,4,5,6,7,8,9,10,11,12,13:All documentation
2=1,2,3,4,5:User documentation set
3=5,6,7,8,9,10,11,12,13

eveloper documentation set
4=6,7,8,12:AutoLISP and Visual LISP documentation set
5=9,10,11:VBA and ActiveX documentation set
6=13:Support Assistance [ASA]
7=0:---
8=1:User's Guide [AUG]
9=2:Command Reference [ACR]
10=4

river and Peripheral Guide [DPG]
11=5:Customization Guide [ACG]
12=6:AutoLISP Reference [VLR]
13=7:Visual LISP Developer's Guide [VLG]
14=8:Visual LISP Tutorial [VLT]
15=9:ActiveX and VBA Reference [AAR]
16=10:ActiveX and VBA Developer's Guide [AAG]
17=11:Connectivity Automation Reference [CAR]
18=12

XF Reference [DXF]
I think you need a 'help' file generator (such as Robo-Help) or such to create the necessary behind the sceens files.
Bob