If you can answer all those and would still be interested in it then that might be the route to go at first.

If you choose to go at it alone, that is fine.

Does anybody at any point had a go at implanting cannabis on their sustenance?

Find an area to focus on and go at it hard.

(Easier said than done, but willing to go at it.)Question boils down to: Should we continue to take advantage of no/low-down owner occupied program everytime we move?

Recently puchased the properties, and it's covered in massive amounts of goat heads, or puncturevines.

NJ is a VERY tenant friendly state, so be careful if you do go at it alone. 

If you go at it start small and see how it goes.

I would take a 2 or 3 quarter view of your average maintenance and see what projections you come up with to be sure the job you'd be hiring for is actually stable on your first go at this. 

As has been mentioned already, if you go at this from the investing side the banks will look at the loan much more from how good is the investment rather than just you.