Hello, Jabrant.
This can be done by a vbs.
[1] You collect all your specially selected wallpaper files (.bmp, .jpg, or else) and put them all in a dedicated folder, say, for instance in the script hereinbelow, I set it as :
c:\windows\web\wallpaper\custom
In that directory, put those picture files and _only_ those picture files, nothing else.
[2] Make sure all your desktop display settings match the requirement of those pictures properly displayed as wallpaper.
[3] Cut and paste the script to a text file named like random_wallpaper.vbs or whatever, and store at some place to your liking.
[4] Make out a shortcut of it and place the shortcut to:
c:\windows\start menu\programs\startup
[5] Upon the _second_ restart thereafter, it would function as required.
Have fun.
regards - tsuji
'------------------------/tsuji/---------
Option Explicit
'--
Edit the location wp_path to your liking ---------
Const wp_path = "c:\windows\web\wallpaper\custom"
Const reg_key = "HKCU\Control Panel\Desktop"
Const reg_name = "Wallpaper"
Dim fso, oFolder, oFiles
Set fso = CreateObject("Scripting.FileSystemObject"

Set oFolder = fso.GetFolder(wp_path)
Set oFiles = oFolder.Files
If oFiles.count =0 Then
WScript.Echo "No custom wallpaper is available." & vbCrLf & _
"Operation Wallpaper setting is aborted."
Set oFiles = Nothing
Set oFolder = Nothing
Set fso = Nothing
WScript.Quit(1)
End If
Dim fIndex, fName, i, ic
Randomize : ic = 0
fIndex = Int(oFiles.count * Rnd +1)
For Each i in oFiles
ic = ic +1
If ic = fIndex Then
fName = i.name
Exit For
End If
Next
Dim wsh
Set wsh = WScript.CreateObject("WScript.Shell"

wsh.RegWrite reg_key & "\" & reg_name, wp_path & "\" & fName
Set wsh = Nothing
Set oFiles = Nothing
Set oFolder = Nothing
Set fso = Nothing
WScript.Quit(0)
'------------------------/tsuji/---------