1. VMG is "overated!" Wow, I'm gonna get some bad mail on that one! Now you tell us you do have VMG... It's great for local buoy racing with marks relatively close together (a mile or two). Mark VMG is great when you get closer to them. It's also a great teaching tool, because it is rare to find even the first upwind mark exactly "in the wind" which was your OP. But you might remember earlier VMG discussions on this board where there are two VMGs: one to the first mark (or destination) and one to the wind, usually measured a few thousand miles out on a projected waypoint dead upwind. What you're essentially asking is how to use VMG going upwind to get there fastest. I have not yet been able to distill 10 years of racing experience into two paragraphs, and while you're not specifically asking for that, it really is the answer, but I'll try: Set a windward VMG, set a mark VMG, sail the long tack first, and account for current and drift and your own leeway.The truth is I could use the nav station mounted GPS for VMG, but I don't think an instantaneous VMG readout is going to inform tactics very effectively.
I like the "20 degree cone" concept. Does that mean a cone extending from the target back towards the starting point, and tack when you reach the cone (for shorter tacks as you near the target)?
2. For cruising, yes. For racing, sometimes not because of #1.
But, as mentioned, conditions usually change during the day.
That's as best as I can sum it up. Just for fun, you might enjoy digging into a yacht racing strategy book, which would give you much more detail and be applicable to your goals.
PS - One of the reason that most sailing websites, being boat-specific or general, do not have "Racing Discussions" is that most racers I know don't give away their "secrets," except in the strategy books I mentioned earlier.
PPS - I admire you for considering sailing instead of motoring directly into the wind. Motoring into a wind is the most uncomfortable way to travel I've ever heard of, including a cross country trip having your mother-in-law in the back seat!
Have a great time.