With the more steeply angled headstock sides, you'll almost certainly need some locking tuners to keep the strings in place. With the flatter sides, you've got possible string interference issues, so once you've settled on the design from the top, I'd work up a side elevation to check the string break angles over the tuning posts and whether you are getting enough vertical clearance of each string above the next tuner.
On number 2, it could be possible if the tuners were staggered, but the strings wouldn't run very straight to the tuners, and you'd certainly have to check on the side angle as to whether the stings would clear each other. But probably best to use a different design.
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