404 errors with wp-admin section on multisite install

I’m testing with two sites in a network setup right now and am running into problems with domain mapping when SSL is enabled, specifically when trying to access the admin pages for the subdirectory site.

I have the following setup (DNS names have been changed):

WordPress network installed, using subdirectories and the domain mapping plugin.
Two blogs:
*dev.main.domain.com – Main blog installed when I initially set up WP
*other.domain.com – Second blog, added through WP as dev.main.domain.com/other and configured to map to other.domain.com using the domain mapping plugin.

I’m using these domains because we’re planning to transition a number of sites into this new WP network, but some sites have DNS names like site.domain.com while others are named site.main.domain.com.

SSL is configured in my Apache config using a wildcard certificate for main.domain.com.

Under the “Domain Mapping Configuration” page, I have the following options selected:
1.Remote Login
3.User domain mapping page
4.Redirect administration pages to site’s original domain

Without SSL enabled, everything works just fine. Browsing to other.domain.com displays the correct blog, and dev.main.domain.com/other also redirects properly.
Once I enable SSL, I can still access the frontend pages, but the login page / admin pages for the subdirectory site are not coming up – I get an Apache 404 error when trying to browse to other.domain.com/wp-admin and dev.main.domain.com/other/wp-admin.

If I disable options 1 and 4 under the domain mapping configuration, then I can get to the admin page for the subdirectory site via other.domain.com/wp-admin but NOT dev.main.domain.com/other/wp-admin. Obviously, I get certificate mismatch errors since the wildcard is for main.domain.com and not domain.com, but I’m not as concerned with that at the moment. I’m just trying to figure out what I’m missing in my config that would cause it to behave like this.

I’m admittedly a little fuzzy on the ins and outs of domain mapping and mod_rewrite, but I’m suspecting that it’s something with how SSL and mod_rewrite are interacting with each other. Any ideas, or am I going about this all wrong? I’ve included my Apache VirtualHost configuration and my .htaccess directives below.

Apache config:

[Code moderated as per the Forum Rules. Please use the pastebin]

.htaccess:

# BEGIN WordPress
RewriteEngine On
RewriteBase /
RewriteRule ^index\.php$ - [L]
RewriteRule ^link([^/]*).html$ rewrite.php?link=$1 [L]

# uploaded files
RewriteRule ^([_0-9a-zA-Z-]+/)?files/(.+) wp-includes/ms-files.php?file=$2 [L]

# add a trailing slash to /wp-admin
RewriteRule ^([_0-9a-zA-Z-]+/)?wp-admin$ $1wp-admin/ [R=301,L]

RewriteCond %{REQUEST_FILENAME} -f [OR]
RewriteCond %{REQUEST_FILENAME} -d
RewriteRule ^ - [L]
RewriteRule  ^[_0-9a-zA-Z-]+/(wp-(content|admin|includes).*) $1 [L]
RewriteRule  ^[_0-9a-zA-Z-]+/(.*\.php)$ $1 [L]
RewriteRule . index.php [L]
# END WordPress