Some cats struggle with leaving their comfort zone, including for food, others will munch happily on whatever is put in their bowl and others may decide one day that what was once a favorite is no longer acceptable for his (self-declared) feline highness. The reasons remain often unclear. In other words, your cat falls into the wide range of “normal”, albeit perhaps a bit more towards the edge of the Gauss curve.
For practical reasons cat owners are often encouraged to switch around cat food brands, types and flavors a bit while the cats are young (and continue that exercise), just to ensure wider tolerance - you never know when one single brand and flavor is no longer produced or even temporarily unavailable. It’s possible for older cats, too, but may be more difficult to teach an old dog (or cat) a new trick.
That said, if yours absolutely doesn’t eat wet food, so be it. I would still recommend to get him accustomed to at least different flavors, if not different brands of dry, just in case. The assumption that cats will pick wet over dry is not necessarily true in my experience. Mine often walks into the kitchen and has a clear plan what he wants and often enough it’s the dry kibble. Never got him to eat wet food from the larger cans, btw. The 100g servings or pouches are ok. (Of one brand, some flavors.)
For the teeth part, remember that cats’ teeth are not suited to grind food like we humans do. They are designed to just rip off pieces of their prey and to crack bones. Food is not chewed to a mush, but swallowed in comparatively large pieces. Chewing pieces of kibble is optional for cats and toothless cats manage just fine. I would worry more about other side effects of bad teeth (like infection and pain and the stress from vet visits) than food.
And for pills, you may also need an individual solution. I was originally taught to give pills by holding the cat and pushing the pill relatively far into his mouth. Which obviously resulted in a wrestling match, a pill on the floor and a sulking cat. A dab of malt paste or liver wurst on the other hand makes him swallow his meds without batting an eye. Be careful with the grind-and-mix method. First, not all pills should be ground, second, the more sensitive specimens may detect the “off flavor” and not eat anything. Even if it gets eaten, you want to make sure that the cat eats the whole dose, so it’s tricky for cats with fluctuating appetite - and illness may cause that - and multi-cat households where you need to manage (i.e. avoid) food sharing or theft.
