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Unless you have a goatee, you just need the thing all the way on the right. It helps line up trimming your cheeks and neck line. You use your ears and the corners of your mouth to make everything symmetrical. You can Google beard shaping tool to find one. I use this one.
Oh man, same. I touch up that part* of my cheeks every 3-4 days. I’m lucky enough that they don’t grow too much so I know where to shave them. Sorry I can’t be of much help there :/
Luckily there are things like this now.
Edit: But man, if you are letting it grow from scratch invest on beard oil it helps with the itch you’ll get. Don’t worry about the look so much until you hit the 2nd month mark, depending on how fast your beard grows.
Also after a shower I usually brush my sides up to see the length of it from the upper lip to the sideburns and if it’s too long that’s when I decide to trim it.
Get a beard guide on amazon it’ll make your life a lot easier bro. It helps keep it lined up and even cause without it I tend to go low like you now I just have it at the very top cleaned up the cheek stragglers. But it’s so much easier than eye balling.
The BEARD BLACK Beard Shaping & Styling Tool with inbuilt Comb for Perfect line up & Edging, use with a Beard Trimmer or Razor to Style Your Beard & Facial Hair, Premium Quality Product https://www.amazon.com/dp/B01N5OT49P/ref=cm_sw_r_cp_api_i_WWY4GRRMWSCQQXMYZR53
Similar to this. Really saves time shaping haha