CSS insertion order not respected after views_plugin_cache->restore_headers()

I'm using Drupal 7.10, an Adaptive Theme subtheme and having a Views block with caching in a side bar on my site.

Caching configuration of my block:

Block caching: Cache once for everything (global) 
Cache: Time-based | 1 Hour/1 Hour 

Adaptive Theme adds in adaptivetheme_preprocess_html() a generated CSS file with drupal_add_css(). The generated CSS file is added after the base layout file. This generated CSS file should overwrite the base layout settings.

However, the generated CSS file gets a lower weight than the base layout file due to views_plugin_cache->restore_headers(). This function readds all existing CSS files with drupal_add_css().

The weight calculation of drupal_add_css() is:

$options['weight'] += count($css) / 1000;

During the CSS readdition of views_plugin_cache->restore_headers() the count($css) remains constant and count($css) / 1000 weight is added again to all CSS files inserted until now.

CSS files which are added after views_plugin_cache->restore_headers() do not have a "double weight", i.e. they get a smaller weight. drupal_get_css() outputs them first. But this is wrong. The CSS files should be outputted in the order of insertion.

Example:

1. CSS files are added by drupal_bootstrap() with drupal_add_css():

     4: _drupal_theme_initialize() (Array, 2 elements)
     3: drupal_theme_initialize() (Array, 2 elements)
     2: _drupal_bootstrap_full() (Array, 2 elements)
     1: drupal_bootstrap() (Array, 2 elements)
     0: main() (Array, 2 elements)
Called from includes/common.inc, line 2882   

Weight calculation:
count($css): 1
sites/all/themes/adaptivetheme/adaptivetheme/css/at.layout.css before => weight: 0
$options['weight'] += count($css) / 1000;
sites/all/themes/adaptivetheme/adaptivetheme/css/at.layout.css after => weight: 0.001

2. CSS files are readded by views_plugin_cache->restore_headers() with drupal_add_css():

    16: views_plugin_cache->restore_headers() (Array, 2 elements)
    15: views_plugin_cache->cache_get() (Array, 2 elements)
    14: view->render() (Array, 2 elements)
    13: views_plugin_display_block->execute() (Array, 2 elements)
    12: view->execute_display() (Array, 2 elements)
    11: views_block_view() (Array, 2 elements)
    10: call_user_func_array() (Array, 1 element)
     9: module_invoke() (Array, 2 elements)
     8: _block_render_blocks() (Array, 2 elements)
     7: block_list() (Array, 2 elements)
     6: block_get_blocks_by_region() (Array, 2 elements)
     5: block_page_build() (Array, 2 elements)
     4: drupal_render_page() (Array, 2 elements)
     3: drupal_deliver_html_page() (Array, 2 elements)
     2: drupal_deliver_page() (Array, 2 elements)
     1: menu_execute_active_handler() (Array, 2 elements)
     0: main() (Array, 2 elements)
Called from includes/common.inc, line 2882   

Weight calculation:
count($css): 41
sites/all/themes/adaptivetheme/adaptivetheme/css/at.layout.css before => weight: 0.001
$options['weight'] += count($css) / 1000;
sites/all/themes/adaptivetheme/adaptivetheme/css/at.layout.css after => weight: 0.042

3. The generated CSS file is added by adaptivetheme_preprocess_html() with drupal_add_css():

     7: adaptivetheme_preprocess_html() (Array, 2 elements)
     6: theme() (Array, 2 elements)
     5: drupal_render() (Array, 2 elements)
     4: drupal_render_page() (Array, 2 elements)
     3: drupal_deliver_html_page() (Array, 2 elements)
     2: drupal_deliver_page() (Array, 2 elements)
     1: menu_execute_active_handler() (Array, 2 elements)
     0: main() (Array, 2 elements)
Called from includes/common.inc, line 2884

Weight calculation:
count($css): 41
public://at_css/bergamotte.responsive.layout.css before => weight: 0
$options['weight'] += count($css) / 1000;
public://at_css/bergamotte.responsive.layout.css after => weight: 0.041

The weight of public://at_css/bergamotte.responsive.layout.css (0.041) is smaller than sites/all/themes/adaptivetheme/adaptivetheme/css/at.layout.css (0.042). That's not OK. The order of insertion is not respected.

In my case the layout of my site is broken due to the wrong CSS files order (see #1390750: Main column sometimes narrow).

Adding CSS files in hook_preprocess_html() with drupal_add_css() seems to be OK since Bartik and Garland do it as well.

There's a workaround. The weight attribute can manually be increased in the drupal_add_css() call in the hook_preprocess_html() hook (Example in #1390750: Main column sometimes narrow). Thus, such a CSS file is output later.

Context information: Issue #92877: Add numeric weight to drupal_add_css added the Drupal core weight calculation.

I don't know how a proper fix looks like.