Let's Encrypt is fully automated and will issue certificates as long as you provide an email address AND have a proper, working config. Don't get stuck on that email "issue", your problems will lie somewhere else.
As always when problems arise: check the log files.
Swimming apparel is explicitly made from slightly thicker and very different material, keeping you from looking like you entered a wet-tshirt-contest. That alone is a big subconscious help. Or are you talking about the amount (or rather lack) of clothing?
Eh, most likely yes.