Would love advice on how you all maintain your bookkeeping, yearly filings, meeting minutes, etc.

Until about a year ago we were using a bookkeeper to manage our books in quickbooks.

This is more of a general bookkeeping post, but you may find some similarities and things you can use You can do this manually with five file folders, or a press board classification folder. 

what is a reasonable amount to expect to pay a book keeper or CPA to do my books once a month?

It should strive to become and remain proficient in its field and be competent to properly address issues which arise in connection with the ownership or collection of debts.CANON 3 – CONFIDENTIALITYAn RMAI Member shall always demonstrate their commitment to maintaining the confidentiality of consumer account data which shall be revealed through the development, implementation, monitoring, and annual review of security measures adopted for its protection, not only while having title to the receivable but also during transmission of the data occurring during the sale or purchase of the receivable.Commentary:A Member shall strive to implement the highest standards of information security policies, safety, and security plans and guidelines which meet or exceed any state or federal statutory and regulatory requirements for the safeguarding consumer personally identifiable information and account data.A Member shall abide by all non-disclosure and confidentiality agreements with the parties with whom it has business dealings regarding the other parties’ consumer accounts, proprietary business information, and trade secrets.The obligation to protect confidences does not preclude a Member from revealing information when consent is provided; as permitted in statute, regulation, or case law for the collection of a debt; or when required by law.It is not improper for a Member to give, as allowed by law, limited information from its files to an outside agency necessary for statistical, bookkeeping, accounting, data processing, banking, printing, or other legitimate purposes, provided it exercises due care in the selection of the agency and warns the agency that the information must be kept confidential along with the execution of proper confidentiality agreements.CANON 4 – COMMUNICATIONSAn RMAI Member shall demonstrate caution in its verbal and written communications with others which shall be revealed through the absence of false, fraudulent, misleading, deceptive, or unfair statements.Commentary:A Member shall accurately represent professional memberships, designations, credentials, capabilities, and experiences.The name under which a Member conducts its business should not mislead others concerning the identity, responsibility, and status of the Member, even if such name is permissible under the FDCPA or other state and federal statute.A Member shall not directly or indirectly compensate or give anything of value to representatives of the press, radio, television, or other communication medium in anticipation of, or in return for professional publicity in a news item unless such payment is disclosed in such news item.

Insurance, bookkeeping, misc.  

If the flooring is bad you should pay to replace it if for nothing else to keep bookkeeping records simple.

What are the book keeping and occupancy tax challenges that are faced?

More than half of that is accounting, pay a bookkeeper $100/mo and you should be working less than 10 minutes per week. 

We also use Stessa for bookkeeping For our recently launched, out-of-state, short-term rental (STR), we use OwnerRez to manage the property AND our Schlage Encode WiFi locks, Honeywell WiFi thermostat, PriceLabs for dynamic pricing, Touch Stay for our digital guidebook (which has answered nearly 100% of guest questions), Thumbtack for handyman services, and Turno for cleaning services.