This is makes a lot of sense to me. NYC has some of the great wine stores in the world. Don’t know all of them, but I bet stores like Chambers Street, Crush, Morrell’s etc., could put together a case anytime you want it that would provide diversity, value and no shipping costs.
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I am a club member or mailing list member at several Oregon wineries. There are a very select few that will let you customize your order. As previously mentioned, Patricia Green Cellars is one and the others would include Crowley and Goodfellow. PGC and Goodfellow offer a 20% discount with discounted or very reasonable shipping rates to the east coast. Crowley offers a 15% discount and free shipping with the 12 bottle club option. I’m not sure that anyone can meet all of your criteria, but I highly recommend all 3 for delicious wines and wonderful peeps.
I know that Andrew Will wines are widely available, but I would suggest joining the mailing list for special offers that will meet a lot of your criteria.
Rasa Vineyards has a couple of club options with discounts. Some of their wines are in your price range and they have some great package specials throughout the year. They’re also real nice guys and have some good Zoom sessions discussing their wines.
I have a general dislike of wine “clubs”. I much prefer to get an email once or twice a year telling me I can buy a few wines… I am then in the driver’s seat. But I have signed up for numerous winery clubs over the past couple of decades. Some were better than others. The best one to date was Adelaide. What I liked about this particular winery-based club (as opposed to a retailer of several), was my ability to alter the automatic shipment. I’d get a notice to log on to my account and make changes to the next shipment. They also had good discounts and very reasonable shipping fees. And, they make great wine at good price points. https://www.adelaida.com/
A retailer-type club that I belonged to many years ago, was Brix26. When I was just getting into wine, I had no clue what to buy. I stumbled onto this wine shop and the owner (Peter Langenstein) built a custom profile for me and wines he thought I might like to try. Then every six months or so, I’d get a case of mixed wines shipped to me (west coast wines). He gets access to some pretty hard-to-get wines, and I don’t know what mojo he used to get them either. Might be worth a look… https://www.brix26.com/