Your question has several parts so let’s take them individually:
Regarding the neighboring road association’s difficulty obtaining liability insurance, that particular RA should have pointed the agent to the Private Ways Act which gives owners along private roads specific procedures to form an association that has the right to assess and collect assessments for the maintenance of the road. Liability insurance is specifically included as an allowable cost (Maine Title 23 §3101.9). The act does not require road associations to register with the state, but it does provide statutory authority for its existence. Perhaps the insurance agent was not aware of this so in the future please feel free to contact MARA for assistance.
Regarding EIN requirements: Provisions of the Patriot Act of 2001 contains “Customer identification program requirements” for most banking institutions. As a result, banks require (among other things) a tax identification number (social security number or employer identification number) to open bank accounts.
Regarding filing tax returns: The short answer is yes; road associations are required to report income to the IRS on one form or another. The IRS recognized that homeowner associations (which loosely includes road associations) do not fall nicely under any of the many paragraphs in IRC §501 permitting tax-exempt organizations. So, in 1976, the Internal Revenue Code was amended to include §528 which allows certain organizations to choose to be treated as a qualifying homeowner’s association and be taxed in accordance with provisions of that section. For those organizations, IRS form 1120-H is the proper form to use to report income. From the IRS website: “If the association does not elect to use Form 1120-H, it must file the applicable income tax return, for example, Form 1120, U.S. Corporation Income Tax Return.”
That may be the rule while not being the practice for small organizations if only because, for most road associations, expenses equal or exceed income, and dues and maintenance assessments are exempt forms of income under §528, so no tax is due, and no one likes useless paperwork.
Regarding 1099 NEC’s: The IRS treats businesses, nonprofits and HOA’s (and thus road associations) the same when it comes to issuing 1099 forms, it is a requirement. From the IRS website: “For more information regarding reporting non-employee compensation and exception to reporting refer to the Instructions for Forms 1099-MISC and 1099-NEC “
Disclaimer: Having said all that, the Internal Revenue Code is extremely complex as are instructions issued by the IRS and issues may mot be exactly as they appear on the surface so each organization should consult with an accountant or tax attorney with experience on these issues to determine the appropriate course of action for their organization.