Good call on the electric fencing. As you are finding out, putting the theory into practice takes some thought and effort.
How big of an area are you enclosing? Square feet or acreage?
On the wire, I have found the 17 gauge aluminum to be as effective as the 14 gauge steel, and a whole lot easier to work with. At least for small areas. On solidly braced corners, I end a run with donut insulators tied to either steel posts or wood posts with a wrap of wire. Hot wire just gets a couple turns around the donut and a few turns back on itself.
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To tension your runs, use ratchet style tighteners (correct term is strainers). Anyplace (TSC, etc) that sells E fence supplies should have them. How many depends on how long of a run you have. I have these on one end, and another set out in the middle and they will keep my runs from sagging over distances of about 400 feet total length, and that is through two turns at the corners. (This fence is only 3 sided......so two terminal corners and two turning corners). For long straight runs, a single strainer located in the middle of the run should tension up a few hundred yards with no problems. For long straight runs, I'd go back to 14 gauge steel, as there is no need to turn the corners and it will stretch less and be more durable.
For straight runs in the range of several hundred feet and longer, I also like the notion of using barbed wire. It is pretty cheap (cheaper still if you buy used on Craigslist) and not so tough to work with and is durable. When fencing in acreage sized fields of corn stalks for cattle to graze in winter, that is all we used. I hadn't considered the advantage of the barb tips getting through the fur, but it would certainly do that. Tension those with regular fencing wire stretchers.
For smaller areas, polyrope or polytape will also work, and even longer runs of several hundred feet of that can be tightened by hand. Polyrope or polytape are also more visible for bears, who apparently don't see as well as some predators do.
I don't have any gates, but the simple way would be to isolate an insulated electric grid on the gate itself that you can shut off with a throw switch or spring loaded gate connector. Or, if you think you can manipulate the gate latch without getting zapped, just leave it hot.
As for grounding in dry conditions, I think you are on the right track as far as using your voltmeter to test it. If you have good ground rods at the fencer, your voltmeter out on one of the runs should tell you if you getting a good zap. Do put something down that would mimic a bear's paw......say a small can with water. Touch the ground part to the can's edge and probe to the fencer. If you get nothing, bear wouldn't feel it either. If you do find good voltage, he would too.
BTW, there are lots of ways to enhance your grounding other than pounding in a bunch of ground rods. You could also connect your ground wire to a chain link fence or even a long run of livestock fence built with barbed or woven wire. That way each steel post becomes part of your grounding system. Also, if you already have an existing wire fence, and the E fence is going to be hung outside of it, can you also ground the existing wire fence? It is probably already grounded to some extent, but you can hook up to it too? In really dry conditions, the more grounding the better.
Hope this helps!