Deleted E-mails return + sync help.

Hope there is some help out there? I have tried to read the posts on this issue but have found nothing to address my particular issues...so here goes:
1) I am using outlook and sync'ing the e-mails through the POP server.
a. Following reading an e-mail, I press the "Delete" key - which sends it to the "trash" folder (not really "deleted").
b. Sometimes the deleted e-mails return as "unread". How do I stop this from happening?

1b) How can I automatically "empty" my trash folder? (in Outlook, I select to "empty" my trash folder upon exiting Outlook) ...or alternately, can I "select all" e-mails in the trash folder and delete?

2) Is there a way to sync Outlook e-mails to my DROID so what I read shows read (in Outlook or on my DROID) and what I delete is also "sync'ed" ?

Thanks in advance for your help.....