Devilfish,
Not sure who your head porter is so can't comment on the comparision of heads vs. 107 kit and best bang for buck. If one of the following guys is your porter:
John Sachs, WFO Larry, Dave Mackie, Bob Wright, Dan Basiley, R&R (Reggie), or Poorboy (Ron Head) then I would say surely go for headwork.
More cubes are only as good as the heads that are on the bike since your only going up 4 cubes from a 103 to 107, imo I would spend money on the heads than later come back with larger juggs and pistons (107 kit) if necessary.
Depending on year of your bike, you might be better served getting the heads done correcting any issues like pistons in the hole, making sure your cylinders are truly round top middle and bottom setting the CC's and squish correctly to optimize your build. Having the right size intake and flow won't hurt you either. I wouldnt do headwork and not check the cylinders, piston to wall clearances and roundness.
Good luck with the build