I had a couple of hours spare this evening. Previously I've had issues running an x86 chroot. I've tried several known working directory hierarchies which chroot should work with. I've even tried an x86 chroot binary. So continuing down the LD_LIBRARY_PATH and ./ld-linux.so execution route I decided to try the exact instructions that worked in 2004 on PPC, old RedHat RPMs and wine version to guarentee old non NTPL stuff.

Unfortunately I think I've hit a blocker:

~/winefiles $ ../qemu-i386 -L /home/user/winefiles/l lib/ld-2.3.2.so usr/bin/wineserver
~/winefiles $ ../qemu-i386 -L /home/user/winefiles/l lib/ld-2.3.2.so usr/bin/wine-pthread notepad
Could not stat /mnt/floppy (No such file or directory), ignoring drive A:
err:dosmem:setup_dos_mem Cannot use first megabyte for DOS address space, please report
err:heap:HEAP_CreateSystemHeap system heap base address 0x65430000 not available
Segmentation fault

~/winefiles $ ../qemu-i386 -L /home/user/winefiles/l lib/ld-2.3.2.so usr/bin/wineserver
~/winefiles $ ../qemu-i386 -L /home/user/winefiles/l lib/ld-2.3.2.so usr/bin/wine-pthread pscp.exe
Could not stat /mnt/floppy (No such file or directory), ignoring drive A:
err:virtual:map_image Standard load address for a Win32 program (0x00400000) not available - security-patched kernel ?
wine: could not load L"C:\\windows\\pscp.exe" as Win32 binary
~/winefiles $

I need help from a qemu/wine/armlinux/kernel expert to continue.