When are 1099 Forms needed for 2023 and 2024 taxes?

[Becca F.]

Three questions:

#1: I have a small time property manager. Is he required to issue me a 1099 form for rental income for 2023 taxes? If yes, what kind of 1099 Form. My larger PM companies issue me 1099 forms with gross rental income? Is that correct?

#2: If I had work done by a contractor who was Incorporated (e.g  ABC Construction, Inc) of over $600 do I need to do a 1099 for him? Someone told me no since he's incorporated (I guess if it's a C-Corp or S-Corp??) I paid him by check. 

#3: If I had work done by a contractor who is an LLC (e.g. XYZ Contractor LLC), of work over $600 do I need to issue a 1099 for him? If yes, what kind of 1099 Form? I paid by credit card.

I didn't have either contractor do a W9 and I don't currently have their EINs.

I don't have a CPA yet. I do my own taxes.