First. I wanted to thank everyone for their good suggestions and input. That got me thinking about the "hole in the box" problem.
I'm a hardcore engineer and hence I am over-analyzing this situation I've been putting a lot of mental effort into the outdoor setup so that I don't have to return to it anytime soon for repairs or water infiltration.
Second, the problem is that I am not using a dome camera with a sealed base but rather some EmpireTech T5442T-ZE and TM-AS-S3 models which have an open base. That leaves the large hole in the box open to the outside unless I come up with a way to adequately seal it.
Third, I have 5+ boxes to play with and hence I can try using (1) duct seal, (2) caulking and (3) Alaska Country's interesting suggestion of the "NM/SE clamp connector" + 1/4 inch ID vinyl tubing (that is something I should have thought of myself!). I think all 3 suggestions are equally good. I have yet to mount the cameras but was awaiting all of this feedback before pulling the trigger.
However, I was concerned that the duct seal might fail in the harsh outdoor environment, as two cameras will be south and south-west facing and hence can experience -30C to +30C temp swings throughout the year.