With the rate Form 4's have been getting approved recently (3 weeks), it definately sounds like there is an issue.
When I made my first NFA purchase, I asked to see a copy of the Form 4 first. I then confirmed that the NFA item was "in the system" and to "whom" it was registered. Also confirmed his address, phone number and employment information before sending him the big bucks. Half up front, half after approval.
________________________________________________________________________________
Has his check cleared ? That usually occures within 10 days of the paperwork being sent.
Have you seen his Form 4 ?
Is the item registered "in the system" ?
Hows about having him fill out another form 4 and then, have him send it to your dealer (for completion) instead ? That way you know it gets sent to Chicago. Might be worth having you pay the first tax and then, get reimbursed on the back end of the deal.