I recommend trying a test to make sure that ListMail can send to your addresses. Set up a test list and put some of your addresses on it (Hotmail, Personal, etc).
Next, modify admin.php to output additional SMTP debug information. Search for the following:
// debug, shows SMTP messages
// $bugs = '1';
And change it to read as follows, uncommenting the $bugs variable:
// debug, shows SMTP messages
$bugs = '1';
Then, try a test email to your test list and see if there are any messages that indicate ListMail might be incorrectly sending email to your SMTP server.
The only thing is, even with SMTP enabled welcome and confirmation messages are still sent with Internal PHP mail(). This is done to prevent too many connections to the SMTP server in case of many signups. SMTP is, however, much faster and more reliable for larger list email.
Even though welcome and confirmation messages are sent with internal mail there could be a response in the SMTP debug messages that tell us why your messages are not being delivered to your personal addresses.