Tax Implications: Paying Airbnb cleaner via Venmo

[Account Closed]

Hi All! 

In Feb 2022 I bought and started managing my first airbnb. It has done well this year! But now that tax season is upon us I have a few concerns...

- My cleaner was paid about $9k via Venmo(this was a personal account not a business account). Will Venmo send her a 1099k automatically? If I deduct this expense on my taxes will I need to send her a 1099 or does venmo do that? I have seen on the forums if money was sent via credit card/ach a W-9 from the vendor is not needed. Is this correct?

- I was not the best at recording mileage... I am going to estimate. How much of an issue is this?

-My home depot receipts were being sent to an email I no longer have access to. Does anyone know if Home Depot can just send me receipts If i provide the card used???

Also - I have an accounting background and I use quickbooks online.

Thanks!

Sarah