Does holding rental in LLC trigger 1099 filing requirement?

[Susan Herschell]

Hoping somebody with strong RE tax knowledge can help resolve this question!! This is the first year we have held a rental property in a multi member LLC (our other rental property is held personally). We self-manage both properties on the side because they have long term tenants and are pretty low maintenance. However, as we don't qualify as real estate professionals (not working close to 750 hrs per year etc.), we haven't filed 1099s for contractors in the past. However, I am now trying to confirm whether holding the property in an LLC with separate EIN (that contractor payments were made from) has any bearing on whether we are required to file 1099s for the LLC property expenses? Our CPA thinks it is a gray area for the property held in the LLC but I am wondering if anyone with more RE specific tax experience has had this question answered conclusively. Thank you guys!