Do not buy 100 of a single brand of razor before trying them out to see if you think they're comfortable on your skin. Most blades will only give you 2-4 3-pass shaves and no two blades are quite the same. Buy a sampler pack and see what you like (warning, feathers have a reputation for cutting through things like they're not even there), then make your first 100-blade purchase once you're both comfortable with your new routine and understand what your skin reacts to.
Probably not. Wet shaving's benefits are largely in the cost vs shaving daily with disposables, plus you've gone from a 30 second shave to likely a 10 minute one. I do like the way my skin feels after a wet shave much more than after a normal convenience shave.
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