From what I can tell the fees per booking are high and they don't really cover much other than those extras if I don't like the actual combined utility of the calendar maintenance of airbnb and vrbo.  

For those who have a hot tub for your rental, may I ask how much you schedule maintenance and how much you pay for that maintenance?

Besides comprehensive lease agreements outlining the tenant’s property maintenance and damage prevention responsibilities, I am also thinking about signing with a tenant's additional agreement with all prices for typical damages which they need to sign with a lease.

Assess if you have enough time for tasks like tenant screening and maintenance.Expertise: Professional managers know landlord-tenant laws and property maintenance best practices.Cost vs. benefit: Weigh management fees against potential savings and efficiencies professionals might offer.Property location: Distance from your home to the property matters.Number of units: More properties increase management complexity.Stress tolerance: Consider your comfort level with tenant interactions and problem-solving.Long-term goals: Professional management can free you to focus on expanding your real estate portfolio.

I have a main tenant who brought over a guest that has been living with the main tenant for ~6 months without permission from me (the landlord).

Are these needing more maintenance than other areas where there isn't so much rain and now. 

I currently have QuickBooks, but I'm not sure if it is possible to incorporate maintenance requests/ticketing, late payment notices, and other landlord specific tools.

You can also hire a company simply for cleaning and maintenance, but you will be actively managing them, communicating with the guest, scheduling the cleanings and repairs, etc.

Also, define how you'll share the acquisition costs, such as the down payment, renovation, and closing costs.Payment Responsibilities: Explain how to divide and pay for regular costs like mortgage, property taxes, insurance, homeowners association fees (if applicable), and upkeep expenses.Management and Maintenance: Agree on how property maintenance, repairs, and improvements will be handled, including decision-making processes, funding for these activities, and responsibilities for performing or managing the work.Single Decision Point: For example, I've seen situations where one person agreed to replace an appliance while another strongly opposed it.

That's why certain areas seem like great deals, when in fact, you have so much deferred maintenance and inability to collect rentsGino