Then, after booking, I send a more detailed version to cover important details like noise, extra guests, and check-out procedures.Since you're in a vacation market, setting clear expectations upfront while keeping the details for later might be a good balance.

Right now we're inquiring with our insurance provider to validate proper coverage, checking with our rental license if it covers uses like this, and working through what a lease would look like. 

I'm assuming you have one lease covering both tenants and not individual leases.

This means for larger ticket items they will cover some maintenance or repairs on them. 

and also like what I do Utilize as STRs: You furnish and list these properties as short-term rentals (STRs) on platforms like Booking.com or Airbnb.Generate Cash Flow: The higher rental income from STRs, compared to long-term rentals, allows you to cover your mortgage/lease payments, generate positive cash flow, and potentially have funds left over for further investments.Positive Cash Flow: STRs often generate higher rental income than long-term rentals, allowing you to cover your costs and potentially profit.Tax Advantages: You can often deduct expenses related to your STR business, such as mortgage interest, property taxes, and maintenance costs.

The question I have is, if I get a hard money loan, can I get enough to cover the closing costs and realtor fees and other associated fees?  

My tenants will cover the mortgage plus $300.

- Guest Insurance – Do you require guests to carry their own insurance, or do you use a service like Safely, Proper Insurance, or another option to cover damages?

>The likely rent I'd get in this area will cover half my mortgage payments at the momentI have done all of my brrrr in different market and I have the same issue that after a refi to extract the value add, my high LTV property at current rates is large cash flow negative (not as large as only covering 50% of the mortgage).  

https://www.amazon.com/couch-covers-pets/s?