I recommend that you research the "Martin Ice Cream and the sale of personal goodwill" . This an option for seller which you could offer negotiating a price reduction due to the potential tax savings to the seller.

I have experience with personal goodwill, which is primarily used in a C-Corporation selling assets context to minimize sellers taxes on an exit (avoiding double taxation). Buyers are typically indifferent to the tax position of the Seller on this topic, but Buyers needs to make sure they are protected from any taxes that have successor liability in the event the Seller's personal goodwill position is not sustained on audit . Martin Ice Cream is the court decision that paved the way for the personal goodwill position/argument. There are hundreds of personal goodwill court cases out there and they fall into the category of bad facts and the taxpayer looses and good facts and the taxpayer wins. Sellers that use the personal goodwill position need to pay special attention to all of the factors developed by the courts and make sure they closely align to the favorable facts and have few unfavorable facts. In addition, there are some administrative things that are important to Sellers to document properly in the transaction documents, that are often overlooked. If you want to discuss further send me an email and we can set up a call to discuss. redacted