I can appreciate that you like the second answer better ( much, much less paperwork for ExpertAsk), but I seriously doubt IRS
would accept the Joanacpa's answer.
My account with ExpertAsk represents a payment that will come from ExpertAsk, not a payment that will come from a variety of payers (a variety of sources, yes), but ExpertAsk is receiving funds from these sources and depositing them in an ExpertAsk account (correct?). At this point ExpertAsk has complete possession and control over these funds. Correct? It is ExpertAsk who will disburse these funds, subject to the instructions of the various participants (instructions established by ExpertAsk). The participant does not make the payment to the expert, ExpertAsk does!
My perspective. Funds paid to ExpertAsk are Gross Revenue of ExpertAsk. Payments to experts are sub-contracting expenses of ExpertAsk, subject to 1099 guidelines.
Further, it is not reasonable for IRS to expect that various participants to obtain SS# XXXXX various experts and track payments. ExpertAsk is in a position to obtain this SS# XXXXX track payments. It is EASIER for IRS to enforce 1099 requirements at the ExpertAsk level than at the participant level.
Andy, if I were your tax advisor, with an interest
in protecting your best interest, I would advise you to track the payments and issue 1099s for them. It is SAFER for you!
AND, I would be hesitant to give my SS# XXXXX a multitude of participants who MAY need to issue me a 1099. If participant issuance of 1099s would be the correct avenue, part of the expert registration would be to provide SS# XXXXX have that number given to any participant who wanted to "accept" an answer. This is too wide a scope of SS# XXXXX To provide ExpertAsk with SS# XXXXX XXXXX a problem at all.