My barber accepts only cash or checks made out to "Cash".
Is there a likely legitimate reason she might want the checks made out to "Cash"? Or am I helping her hide her revenue from the IRS?
There are legitimate reasons:
I wouldn't jump the gun and assume that this person is avoiding taxes, etc. Barbers are usually licensed professions. Since it's generally a cash business, they tend to get audited more often by the tax authorities.
That said, I wouldn't pay her with a check -- you have no idea who is actually cashing the check, and you could run into issues with unknown third parties misusing your account information.
There are benefits associated with a cash only business (the link states a few). However checks made out to "cash" don't reap those benefits listed. For anyone on SE to say your barber hides revenue from the IRS would just be speculation.
With that said there are a great number of disadvantages for a cash only business. And from my experience, a business that goes out of their way to take cash only can be a little suspicious. Luckily you are not committing any crimes or fraud by paying her cash.
To put a positive spin on the whole thing, maybe it's a small family shop, and having the check made out to "cash" means that your barber can hand it to someone else without the need to countersign.
Or maybe his last name is "Cash" - there was a pretty famous singer who fit that description.
Either way, it's not your place to nanny his finances.
They're hiding income.
The IRS is a likely candidate for who they are hiding it from but not the only option.
Another possibility that comes to mind is someone who had a judgment against them--a check made out to "cash" could be handled by someone else and thus not ever appear in their bank accounts.
If the business owner doesn't want you to pay him directly, the only reason I can think of is breaking a law. It can be because the business doesn't legally exists, or because the barber wants to evade taxes, or because he doesn't pay his child support or doesn't want his income to be apparent to his debtors in a bankruptcy proceedings.
Either way, stinks.