How do I add multiple LLC's to the rental real estate enterprise statement or should that just be done at the individual level not the passthrough entity level?

Yes, it does.  You do not have to have multiple properties to qualify.

 

Per the IRS:

Solely for purposes of this safe harbor, a rental real estate enterprise is defined as an interest in real property held to generate rental or lease income. It may consist of an interest in a single property or interests in multiple properties. The taxpayer or a relevant passthrough entity (RPE) relying on this revenue procedure must hold each interest directly or through an entity disregarded as an entity separate from its owner, such as a limited liability company with a single member.

 

The statements you are attesting to are the following:

• Separate books and records are maintained to reflect income and expenses for each rental real estate enterprise.
• For rental real estate enterprises that have been in existence less than four years, 250 or more hours of rental services are performed per year. For other rental real estate enterprises, 250 or more hours of rental services are performed in at least three of the past five years.
• The taxpayer maintains contemporaneous records, including time reports, logs, or similar documents, regarding the following: hours of all services performed; description of all services performed; dates on which such services were performed; and who performed the services.

You then attach a statement to the return filed for the tax year(s) the safe harbor is relied upon.

Is this the first year that we have to file form 199A regarding Rental Real Estate Enterprise Statement? 

how many rental properties do you have to have before required to file form 199A