I am running FreeBSD-3.3-RELEASE. The latest squeak port that
I can find for this OS is at version 2.4. 

The FreeBSD port make file contains

$FreeBSD: ports/lang/squeak2/Makefile,v 1.12 1999/08/25 06:35:29 obrien Exp $
MAINTAINER=     jesse at cs.uni-magdeburg.de

If this maintainer is tuned in to this list or if any one else knows,
is the FreeBSD squeak port being actively maintained? If so when might
it be upgraded to 2.7 or beyond?

In the event that no one has the time to do this, how can I get
there?

Can I run my 2.4 VM and filein some set of changes that will result
in a 2.7 image from which I could generate a new interp.c file
which could be compiled into a new VM-2.7?

What is the magnitude of this task? Is it mostly turning the
crank, or is a thourough understanding of the squeak interpreter
and the target OS necessary?

Refer me to the documentation and I will gladly RTFM.

BoB