Ok, so here's a better grasp of my scenario .. maybe...
Again I have 100 acres , a long skinny pie shape for lack of better terms. Mostly woods, my house/barn/sawmill are in one "field" or opening in the woods, there are two other "openings" one maybe an acre the other maybe 7 or 8. My woods are tall (75-100 ft) pine trees. If I were to want to check that 7 acre field and take off from where my house is that would entail taking off, rising maybe 150 feet to clear the trees in between, going back down in altitude and flying in that field.. then the same thing to return. So when I lower down into that field I would lose VLOS due to the trees in between.
So this is an illegal scenario? Is that the case with any drone or just the ones over that 250gr weight?