When iOS simulator starts, is it possible to automatically load the Web Inspector?

This is a partial solution. This opens the debug window of Safari with one click which is a lot better but not automatic.

Open Script Editor on your mac (Command + Space Bar and type in Script Editor)

Paste in this code:

-- `menu_click`, by Jacob Rus, September 2006
-- 
-- Accepts a list of form: `{"Finder", "View", "Arrange By", "Date"}`
-- Execute the specified menu item.  In this case, assuming the Finder 
-- is the active application, arranging the frontmost folder by date.

on menu_click(mList)
    local appName, topMenu, r

    -- Validate our input
    if mList's length < 3 then error "Menu list is not long enough"

    -- Set these variables for clarity and brevity later on
    set {appName, topMenu} to (items 1 through 2 of mList)
    set r to (items 3 through (mList's length) of mList)

    -- This overly-long line calls the menu_recurse function with
    -- two arguments: r, and a reference to the top-level menu
    tell application "System Events" to my menu_click_recurse(r, ((process appName)'s ¬
        (menu bar 1)'s (menu bar item topMenu)'s (menu topMenu)))
end menu_click

on menu_click_recurse(mList, parentObject)
    local f, r

    -- `f` = first item, `r` = rest of items
    set f to item 1 of mList
    if mList's length > 1 then set r to (items 2 through (mList's length) of mList)

    -- either actually click the menu item, or recurse again
    tell application "System Events"
        if mList's length is 1 then
            click parentObject's menu item f
        else
            my menu_click_recurse(r, (parentObject's (menu item f)'s (menu f)))
        end if
    end tell
end menu_click_recurse

menu_click({"Safari", "Develop", "IOS Simulator", "index.html"})

Once the simulator has opened, click run on your script (you might need to allow the script editor in the settings the first time).

(Optional) You can save your the scripts as an app so that you don’t have to have the script editor open.

(this answer is a more detailed version of Galatin’s previous answer)