The heated vest/jacket decision depends a bit on how much cold or heat you can tolerate. My wife uses a jacket, plus everything else she can put over it. A vest is usually too warm for me, even on low. The nice thing is that it works without the electric as a nice extra layer, as would a jacket. If you plan on electric gloves, I would go for the jacket, just to make the hookup easier. If you wear your riding jacket without the liner (except in extreme cold) the jacket is nice because it keeps your arms warmer. It appears you have a short windshield. A tall one with hand protection would be my first choice of gear, but I would go for the jacket if you run the stock shield. For marginal weather temps in the mid-thirties to low forties, with a tall windshield, I prefer the vest.
As to outer wear, I have both leather and textile, but I prefer the textile for most riding. Easier to ventilate if it warms up, repels light rain, snow, and splash, and the overpants go on quickly, over anything. The leather will cut the wind...but you need full pants instead of chaps. The leather bib type pants are really warm. Also consider technical longjohns as a base layer, knee length socks, and glove and sock liners. Don't forget a good balaclava. A neck gaiter or a turtleneck is a real blessing, too. There are balaclavas that combine a wind-proof neck flap or gaiter. For extreme cold, a one piece suit is the warmest, if you can fit it to your body, but with a 3/4 length touring jacket, two-piece works very well.
My normal winter wear is a Tourmaster electric vest over a single, turtleneck base layer, Tourmaster overpants, knee socks, sock and glove liners, tall (12") boots, heavy balaclava, heavy gloves or heated grips, and a FirstGear Kilimanjaro jacket.
