Originally Posted by uluvbs
A friend offered to sell us system-wide upgrades but United is saying there is no availability to use them on either leg of our trip.
What would you say are the odds that if we buy the vouchers and go on the wait list for business class that we will be upgraded?
I agree with all the comments posted above ^
I'd only add that if your 'friend' is truly a friend and not an e-bay seller, I'm sure that s/he'll be agreeable to not being owed anything if the upgrades don't clear, right?