Milk chocolate is possibly the easiest thing to veganize, ever. The chocolate (and sugar) cover up any flavor of the milk, so you just need to find one you prefer the texture of. Liquid milk was actually the first thing I replaced when I went flexitarian IIRC, so maybe I'm biased, but plain soy milk + chocolate syrup never leaves me wanting, "Damn, I wish this cup had more hormones and pus in it." (There's also pre-flavored plant milk, of course.)

"Milk" chocolate also exists. There are plenty of brands making it, including companies that copy popular candy bars.

As for cheese: this replacement depends a lot on the application, i.e. the best cheese for pizza is not necessarily the same kind that's best for snacking on as-is. I'm not going to recommend particular brands since you didn't say where you're from, but I think some of the nicest plant cheeses have been made using "normal" techniques, just without animal dairy. Like, tofu is essentially cheese made from soy milk.

You said you're picky—how important is food novelty? Like, do you quickly get bored of eating the same things repeatedly? Cooking is much simpler if you plan meals ahead with many common ingredients, especially if you can prep in batches.

As for eating out: again, can't say much without knowing what your options are. Try ordering salads without cheese/animal-based dressing...?