I recently got errors similar to this

libtool: Version mismatch error. This is libtool 2.2.6, but the
libtool: definition of this LT_INIT comes from libtool 2.2.4.
libtool: You should recreate aclocal.m4 with macros from libtool 2.2.6
libtool: and run autoconf again.

This was happening when I wanted to do a "port upgrade gimp2", basically almost anything that needed libtool and automake would fail miserably. Libtool had probably been upgraded at some point and since I don't blanket upgrade everything I didn't notice that it wasn't working. I tried a number of things to upgrade/fix the brokeness.

So I tried doing

port -v -nR upgrade --force libtool

This would rebuild a handful of packages that depended on libtool. Doing this still failed for me, it appeared that autoconf was picking the system versions of libtool, autoconf and automake. This had baffled me for a while since when I echo'd my $PATH it was showing the correct path.

Then it had occured to me to check if macports was resetting/setting my environment before it built a package. After looking at http://guide.macports.org/chunked/reference.variables.html I checked my macports.conf, it turned out that my binpath was just wrong, I had the system paths defined before my macport install. I just commented out the binpath variable and ran a rebuild of gimp2, everything was working again.

I must have changed the binpath for some reason or another at somepoint to fix something else, that something else makes me think it was openssl that was boned.