You seem very green, I would highly suggest finding a property management company to do this for your while you learn the ropes and how things work.However, you can also get a copy of "The Book on Managing Rental Properties" by Brandon Turner, and get some really good information.The main one's to consider are:Background check - totally clear, or will you allow certain thingsEviction history - totally clear, or will you allow if no evictions for last xx yearsIncome Requirement - usually 3x the cost of rentCredit History - totally clear, or will you allow certain thingsPets - yes or no, size, type, number of pets allowed, extra pet deposit/feeAgain, I highly suggest a property manager to assist you with this.

He moved in March 14, 2023 so this will be his first payment after initial rent and security deposit were paid by cashier's check.Thanks in advance!

To me its worth it for the direct deposit but its soul shattering sometimes. 

The PM is still responsible for giving you any monies owed from rent and/or security deposits.

How much capital do you have available, since even if you successfully syndicate a deal, you are still out of pocket for earnest deposit, due diligence costs, formation costs, etc until you reimburse yourself from the raise.

Can I require additional deposit to cover the accidents this animal is going to make?

First, you always wind up being in for more than you budget, always, and two if you are cutting the capital requirement needed close then you can go under and default.Truth be told, to get through a deal and afford: Down Payment, Closing Costs, Holding Costs, Deposit for contractor, taxes, insurance. 

She offered to pay a full rent's payment upfront, along with the deposit, to compensate for her current unemployment.Are there negatives or major red flags that are associated with this that I should consider as I evaluate her application?

That's all costs and deposit fronting.When project costs rise to 200k - 300k, the investors need to be 45k - 60k liquid to get through the same 5 - 6 months.

And if so, what are the benefits of section 8 if the only guarantee is the direct deposit and yearly inspection?