Go from the inside out! Start with shaving an inverse hitler moustache, end up with mutton chops
Beards
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Man! The moustache is the only thing I don't want to shave! It's Movember.
I like 2 but you will look weird for a few weeks, which is why I like it.
Slowly is less impactful. Though my preference would be to go fairly hard so it stands out. Start by shaving your chin and lower lip (keeping side whiskers, sideburns, and moustache.) Then keep narrowing that up into a neat friendly or trimming down into a hulihee then into a moustache. This I think would give you a much more 'transitional moustache' look than aiming at a goatee. You could also go for a horseshoe.
Option 2 - definitely! Friend of mine did it once - looked really good.