I was able to find a few things that helped me. By default the toolbar item is not added to the finder window unless the user drags it in. I was not able to find a way to programmatically add the item to the finder window toolbar.
Add Item to the finder side bar
// Create a reference to the shared file list.
LSSharedFileListRef favoriteItems = LSSharedFileListCreate(NULL, kLSSharedFileListFavoriteItems, NULL);
// Check Items
if (favoriteItems)
{
    // Get CFURL for Application
    CFURLRef url = (__bridge CFURLRef)[NSURL fileURLWithPath:path];
    // Add Item
    LSSharedFileListItemRef item = LSSharedFileListInsertItemURL(favoriteItems, kLSSharedFileListItemBeforeFirst, NULL, NULL, url, NULL, NULL);
    // Release
    if (item)
        CFRelease(item);
}
// Release
if (favoriteItems != NULL)
    CFRelease(favoriteItems);
Code to Remove Item From Sidebar
// Create a reference to the shared file list.
LSSharedFileListRef favoriteItems = LSSharedFileListCreate(NULL, kLSSharedFileListFavoriteItems, NULL);
// Check Items
if (favoriteItems)
{
    // Get Login Items
    CFArrayRef favoriteItemsArray = LSSharedFileListCopySnapshot(favoriteItems, NULL);
    // Loop Through Items
    for (id item in (__bridge NSArray *)favoriteItemsArray)
    {
        // Get Item Ref
        LSSharedFileListItemRef itemRef = (__bridge LSSharedFileListItemRef)item;
        // Get Item URL
        CFURLRef itemURL = LSSharedFileListItemCopyResolvedURL(itemRef, kLSSharedFileListNoUserInteraction | kLSSharedFileListDoNotMountVolumes, NULL);
        if (itemURL != NULL)
        {
            // If Item Matches Remove It
            if ([[(__bridge NSURL *)itemURL path] hasPrefix:path])
                LSSharedFileListItemRemove(favoriteItems, itemRef);
            // Release
            if (itemURL != NULL)
                CFRelease(itemURL);
        }
    }
    // Release
    if (favoriteItemsArray != NULL)
        CFRelease(favoriteItemsArray);
}
// Release
if (favoriteItems != NULL)
    CFRelease(favoriteItems);
Reload Directory in Finder
// Reload Finder (change the word directory to file if updating file)
NSAppleScript * update = [[NSAppleScript alloc] initWithSource:[NSString stringWithFormat:@"tell application \"Finder\" to update POSIX directory \"%@\"",path]];
[update executeAndReturnError:nil];
Code to Enable Extension (bundle ID)
system("pluginkit -e use -i com.mycompany.finderExt")
Code to Disable Extension (bundle ID)
system("pluginkit -e ignore -i com.mycompany.finderExt")