A good high chair holds a baby steady without feeling like a restraint system, wipes clean in under a minute, and sits at a height where you can actually make eye contact across the table instead of talking down into a tray. The tray itself should pop off with one hand while you're holding a half asleep toddler with the other, because that's the test that matters, not how it looks in a showroom.
The honest limits start with space. A full size wooden high chair with a wide base is wonderful at a table that has room to spare, and useless if your kitchen is the kind where two people can't pass each other without turning sideways. Padded seat inserts feel nice for about a month, then they start holding onto smells and crumbs in the seams no matter how often you pull them off to wash. Chairs with a lot of fabric, straps with thick padding, multiple recline settings, all of that sounds like comfort and mostly turns into more surfaces for yogurt to hide in. If you travel a lot, or split time between two homes, a chair that doesn't fold down small is going to annoy you within a week, not a year.
Where this kind of chair really earns its spot is a kitchen or dining room that gets used every single day, not just for holidays, in a house where meals happen at a real table rather than on a couch in front of the television. Wood and plastic combinations do best there because they take the daily abuse without complaint, and a hard, molded seat with no fabric at all is the easiest thing to keep looking decent through the entire stretch from first purees to independent, flinging, somewhat violent self feeding. Smaller kitchens do better with a chair that clips straight onto the table rather than taking up its own footprint, especially through the season when you're hosting more people and need the floor space back. A chair with adjustable height is worth the extra cost if you plan on using it for more than one child, since it can grow from a baby's first solid food right through toddler meals at the same table as everyone else.
Over time, plastic trays dull slightly and pick up a faint stain from tomato sauce and berries no matter how fast you rinse them, wood legs get nicked and dented in ways that honestly look fine once there's a few of them, and any fabric straps will fray a little at the buckle before anything else goes. Wipe the tray and seat down after every meal rather than waiting for the end of the day, and check the screws on the legs every few months, because high chairs get rocked and leaned on more than any other seat in the house. By the time a child is old enough to climb into a regular chair, a well chosen high chair looks lived in rather than worn out, which is exactly how it should look.