No, a higher version number does not = more secure. Red Hat rarely upgrades to a newer version of an app, within a particular version of the distribution. They *do* fix any security holes in the the version that they distribute. There are several reasons for this. Upgrading to a newer release of the software could break things where keeping the same version but plugging holes in that version will not break things (unless there is a terrible mistake, which I can't recall ever happening).
Take Red Hat 9 for instance. It shipped with 2.0.40 patch level 21 which means the RPM is named "httpd-2.0.40-21" and if you are running an Intel/AMD box would have a ".i386.rpm" extension. Now, since Red Hat 9 shipped, apache has had a security patch applied and is now at 2.0.40-21.9.
If you look at the changelog in the httpd.spec file included in the src.rpm you will see this is the 9th patch since RH9 shipped and here are the changes that were made:
* Tue Oct 28 2003 Joe Orton <jorton@redhat.com> 2.0.40-21.9
- add security fixes for CVE CAN-2003-0542, CAN-2003-0789
- return test page for "/+" in default httpd.conf
- add bug fixes for #103049, #105725, #106454
- further fixes for CGI regressions in -21.5 (#103744)
* Thu Sep 11 2003 Joe Orton <jorton@redhat.com> 2.0.40-21.6
- fix for streaming CGIs (#103744)
* Thu Jul 31 2003 Joe Orton <jorton@redhat.com> 2.0.40-21.5
- fix EXTRA_INCLUDES for #92313
- add mod_include fixes from upstream
* Wed Jul 9 2003 Joe Orton <jorton@redhat.com> 2.0.40-21.4
- add security fixes for CVE CAN-2003-0192, CAN-2003-0253,
CAN-2003-0254, CERT VU#379828
- add bug fixes for #78019, #82985, #85022, #97111, #98545, #98653
- install special.mk, fix apxs -q LIBTOOL (#92313)
* Tue May 20 2003 Joe Orton <jorton@redhat.com> 2.0.40-21.3
- add security fix for CAN-2003-0189
* Mon May 12 2003 Joe Orton <jorton@redhat.com> 2.0.40-21.2
- add security fix for CAN-2003-0245
- add bug fixes for #88575, #89086, #89170, #89179
* Tue Apr 1 2003 Joe Orton <jorton@redhat.com> 2.0.40-21.1
- add security fixes for CAN-2003-0020, CAN-2003-0132, CAN-2003-0083
- add security fix for file descriptor leaks, #82142
- add bug fix for #82587
* Mon Feb 24 2003 Joe Orton <jorton@redhat.com> 2.0.40-21
- add security fix for CAN-2003-0020; replace non-printable characters
with '!' when printing to error log.
- disable debuginfo on IA64.
If you run "apt-get dist-upgrade" or "up2date" every night, then your system would be upgraded with these patched versions of the software automatically. Now, if you install from source, or install a 3rd party RPM that is at a higher version number than what Red Hat ships or that is kept up in your favorite repository then if there is a vulnerability found it will have to be updated manually. I don't know about you but I don't like doing things manually if I don't have to and I prefer to have my systems up to date with any security patches. If I had to do it manually then something would surely get missed.
Here are all the latest updated RPMS for Red Hat 9 in the FreshRPMS repository:
http://ayo.freshrpms.net/redhat/9/i386/RPMS.updates/