I can only recall 4 occasions in my long life and extensive travels that I felt that a waiter was both qualified to advise me and his counsel welcomed.....
1. Nice, 1963 - Advisory commentary on European rabbit/hare (Whilst in my youth out here in flyover country, I had dined on Peter Cottontail and tried jackrabbit, only to find it less than appealing, I knew nothing of those wily Uropeens and their ways with rabbit).
2. Livorno, 1965 - Not really a waiter, more a street vendor, able to convince me (with my halting Italian and his lack of English) that "triglie", the humble red mullet, could be a great entree, not prepared in the classic "Livornese" method, but simply bathed in a little olive oil, S & P, then grilled over an open fire of grapevine, served with lemon, bread and local white wine.
3. Arras, 1982 - Traveling with our young daughters (14 & 9) by car in a big loop around Western Europe, the dining room of an old hotel, a grand old waiter, spent time and effort convincing my daughters (French-less) on the virtues of the price fixe menu and the additions he would make to it. So "un-French" as to amaze me. Dessert wasa choice of a chocolate mousse or fresh strawberries. Our daughters wanted both, together. With much attention from the chef at the doors to the kitchen, they got'em.
4. Galatoire's, NOLA, continuing 1955 or so until the mid 90s. Introduced by my grandfather, a picky eater admiring only the simplest of Gulf seafood preparation, a waiter who became my dining adviser for many visits over the next 40 years, until his retirement. It was from him that I learned the concept of arriving at 2PM for "lunch", always ordering only 1 dish at a time, even better when with a fellow diner, never hurry, and that a good waiter understands the preparation of everything on the menu (and is prepared to recommend or reject, based on his evaluation of your likes, dislikes, and habits).
There may be others out there whom I haven't met, but I've sure been displeased with some I have...