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You will each want your own 1099s. When it comes time to file your tax return, you want a 1099 issued with your name and the amount of rent you paid. This way, when you deduct the expense, there won't be any confusion.
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.
I assume you mean the landlord only wants one 1099-MISC issued to him. if this is a business expense, the business will be issuing the 1099-MISC to the landlord. If all three of you are independent contractors, each with your own business, then each of your businesses will issue the land lord a 1099-MISC for the amount of rent each of your business's paid. The landlord has no say in this. Depending on your individual business's, each tenant may have no choice either.
I don't see that the difference is to the landlord really ... one form with all of the rent on it or 3 forms with 1/3 each it is still the same amount. He doesn't even need your forms to fill in his return ... he only needs to report the total rent received even if you never send a 1099.
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