So after sleeping I did the following:
Read the help pages for Helicon Tech ISAPI_Rewrite v3
Turned the plugin on
In Helm: Home > Domains > simeonpilgrim.com > Website Extensions > URL RewritingWrote my rewrite correctly
RewriteCond %{REQUEST_FILENAME} !-f RewriteCond %{REQUEST_FILENAME} !-d RewriteRule .* /blog/index.php [NC,L] <blank line>
Changed my WordPress permalinks to custom
/%year%/%monthnum%/%day%/%postname%/