re: CPA: winery question

No, if you are a winery you manufacture wine and sell your inventory as ordinary income from your trade or business. As for your idea to become an investor in wine so you can buy and sell for capital gains, I doubt the IRS would go for it. First, they would treat the wine as personal assets instead of investment assets. As such you would have to pay taxes on all capital gains you realize from buying and selling wine, but you wouldn't be able to deduct any losses since losses from the sale or exchange of personal assets are not deductible. So investing in wine for as a money making venture has a higher tax cost than investing in real estate.

In your scheme how is the intermediate entity not a wholesaler? Wholesalers do not get to sell for capital gains.