Q. Should he get three 1099s one from each of us or should one of us collect all rent and pay with one check?
A. For tax purposes you each want to pay your share of the rent directly to the landlord and each issue him a 1099-Misc.
That's best for you, but obviously inconvenient for him. You have to make do with whatever you and landlord agree to. You cancelled check/bank records is proof enough for the IRS, but they do prefer a 1099-Misc be issued.
