What the error message is telling you is that the 'entry_password' column is already in the database.
Sorry can't be more help. WordPress has this capability with a standard install.
I upgraded my test blog and it went smooth. Even got my original design broken up into a theme. Very cool. And not hard to upgrade.
Here is a link to detailed instructions of going from version 1.22 to 1.5
Click Here
Also be sure that four you outgoing through you domain that you are authenticating yourself.
Check the box that you SMTP server requires authentication. Then make sure you use your user@yourdomain.exe for the login and the password you created.
That in addition to changing to port 26 should get you going.
Please open a support ticket with the help desk. https://tchhelp.com
I don't know if it's possible if you didn't install it through cPanel, but the support staff would be the ones that would be able to update it if possible.