Pros
The non-managerial staff here is wonderful; lots of lovely people with wonderful personalities and fun stories. Many of the employees here are college-aged or recent graduates working part-time for extra money/funds; all very kind, hard-working, and competent. A handful of the managers are amazing; mostly the younger staff, who can relate to the employees better and have more hands-on interaction with the actual day-to-day happenings.
The work is easy to learn, even with little experience, and, while it can be demanding, the other employees are always willing to help out and take on extra work if you start to feel overwhelmed.
People bring their dogs which, as long as they are well behaved, is always fun. Employees also receive discounts on wine and food, though it's still pretty expensive either way.
The staff always likes to go out for food and drinks after - be sure to join in on the round of tequilas and Queso Blanco Tater Tots at Chimney Rock Tavern. It makes a hard day (almost) worth it.
Cons
This place doesn't really know what it wants to be; it calls itself a winery but functions more like a strange outdoor restaurant, which, to be honest, it is not really prepared to be.
The customers here can be very entitled, especially large parties for bridal showers or birthdays, and things can get intense; it's a lot of people showing up drunk and getting drunker. Be prepared for people getting sick, yelling at you for little things, and complaining about the rules (even when they're clearly stated.) Also, be prepared for people showing up with outside alcohol and being offended when you point out they 'can't actually have that here.' They'll claim that the unmarked container of clear liquid is 'just water.' I can smell the vodka on your breath, Cathy. Dump it out.
The ordering system is simple and efficient, but that won't stop customers from complaining. Alongside the whole 'is this place a restaurant or not,' the owner and upper staff want wine stewards to act more like waiters, despite the unideal setup and staffing situation. This job is demanding and the customers are rude. Also, many of them bring children... which this place is definitely not made for. Warning: they will complain when you tell them you don't carry soda and other child-friendly snacks. And when you tell them not to let their children run around unattended. And when their child ultimately gets accidentally smacked in the face by a food tray when they run into passing staff members.
For a time, one of the managers there was exceedingly creepy and demanding; constantly yelling at certain employees even when they were doing their assigned jobs, 'popping personal bubbles' and giving unwanted physical interaction, and regularly complaining about the lack of work despite not actually working much himself. He had very little experience 'working the front' to begin with, but also couldn't seem to figure out basic actions as well - such as answering the phone or speaking with customers, which means he would often just stand by a ringing phone and loudly ask if 'anyone was going to answer it.' He was eventually let go, but the fact that he was even hired and stayed for as long he did is concerning.
Also, don't pay attention to the 'work hours' - you will stay overtime. Comedy nights are especially brutal and between the customers that refuse to leave and the amount of trash left on the floor, your shift 'til 10pm will turn into 12am. And even then, you might still be dealing with drunk customers waiting for an Uber.
This is the service industry, so it's gonna suck.
Also also, if it storms really badly (like, flood/tornado warning, etc etc ), be prepared to just. Not be allowed to go home because 'well, it may clear up and we have comedy planned tonight.' You will get caught on flooded roads and it will take you an extra two hours to make it home. If you don't crash first. Or get struck by lightning. Or die of a heart attack when the electricity in the main building pops because something else got struck by lightning.