If you limit yourself to the 16-bit subset, you can use manuals that are even older.
And if you give up binary portability and restrict yourself to the source portability which helped sell people on the 8086 and the 8088 to begin with, you can use a manual for an 8080 processor and convert the code to the earliest 16-bit subset, prior to the expansions the 80286 brought.
And if that's too recent for you, you can move to the IBM mainframe series derived from the System/360 architecture, and use layer upon layer of emulation to run software written in the Johnson administration.
Screw diamonds: Legacy systems are forever.