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When sending emails, you choose which "personality" you want to use when sending. A personality is just a way to group together a common set of sending options:
Personalities are useful if you use multiple different email addresses to sort your email (eg a home email address, a work email address, addresses for mailing lists, etc).
The personality display name is for your reference and is what appears in the popup menu on the compose screen. It does not appear in any sent emails in any way.
The compose screen allows you to send SMS's to other people as well as emails. When you send an SMS, the originator phone number that appears on the SMS will be determined by the number you have set on the personality you use.
Personalities only control what addresses you can send from on the web interface compose screen. When you use an external email client to send emails via SMTP, the email sent and the from address used is controlled entirely by the email software.
However using these two checkboxes, you can control some aspects of sending via SMTP. If you send an email via an external email program (which means it uses SMTP), if the From address on the email matches the From address of a personality, then you can control if that email is also Bcc'd to the other people listed in the personalities Bcc address list, or saved to the personalities Sent Items folder.
Note that you can use some magic values to match email addresses. If you put a '*' in the email address on either side of the @, then it will match anything. For instance, *@okmail.net will match any @okmail.net email address you send with. If you have a personality with a specific email address that matches a From address, that will take precendence, * matches will only occur as a fallback. Also note that it's not meaningful to use personalities which have a * in the email address to send from the web interface, you'll probably just end up with a bounced email. The * magic is only to support the SMTP Bcc/Sent Items feature.
The Sent Items option can be particular useful in a couple of different cases.
When setting up a vacation auto-reponse on the define rules screen, the response will only be sent when email arrives to specific email addresses, not all possible email addresses (eg you might have aliases, or addresses in your own virtual domain, etc).
To ensure that a reply is sent to email that arrives at a particular address, you need to add that address as a personality, and make sure the "Use for vacation replies" checkbox is checked.
Note that replies will always be sent for email sent to the address that corresponds to your account name. Also if you have more than one personality that uses the same email address, then if the "Use for vacation replies" checkbox for any of the personalities is checked, a reply will be sent. Also note that the check is only done on the incoming email address, the full name part attached to the email address is not used.