Lets say that an individual, Bob, has a regular job which covers his daily expenses, but also has an illegal side job. A decent percentage of his disposable income is due to Bob's illegal activities, but he has some disposable income coming from his legal activities. Both sources of income are placed into a bank, and bob then makes payments using a credit/debit card.
I'm wondering where the line is drawn for stating that someone has received illegal goods, as there is no longer a way to tell what money was legally earned and what was illegally earned. I'm wondering both in cases in which one is aware of bobs illegal activities and in cases where the receiver of the money does not know it's illegal, but could still be compelled to refund it if it were illegally obtained.
A few examples of the ambiguous situations I can think of:
I assume if Bob buys a single drink at a local bar this would not be ruled as spending illegal money and the bar would not be committing an offense even if the owner of the bar was aware that Bob had an illegal income source, as Bob could easily purchase a drink with his legal income.
Likewise I assume if bob goes out to buy a Yacht that he could never afford with his legal income it would be considered to be purchased with illegal profits.
However, what about a more ambiguous case. If bob buys an expensive fur coat for someone, which he could afford to do with his legal income, but which he likely wouldn't have chosen to spend money on if he didn't have the additional illegal income, does the coat count as profiting from illegal goods?
What if Bob offers a smaller sum of money to many people, small enough that Bob could easily afford to give such a gift to one person, but the combined cost of so many small gifts adds up to an amount bob couldn't/wouldn't have been able to afford without his supplementary income? Could someone argue that the gift they received from Bob came from his legal income, but the other gifts Bob made to others was due to Bob's illegal activities, by claiming Bob was likely to give a gift to them without the extra illegal income but not to the others etc?