Gatlinburg Cabin Post-Covid Rentals

[Arthur Means]

I have done single family rentals in the Midwest and enjoyed it.  Prior to moving to NC for work, Gatlinburg and the surrounding areas are my most frequented vacation destination.

Some background information...

1.  I understand that every month will not be profitable. I am ok with this, but I do generally expect a positive annual cash flow

2.  I don't need the money to live, which is why I'm ok with some months being negative

3.  I work for a Fortune 500 company and receive annual stock awards. I'd like to use these to finance the down payment for this business. 

4.  The end goal would be to have 2-3 fully paid off properties and potentially retire and live off the monthly income (10-15k per month)

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All that being said. I have some very basic questions that I'm hoping someone with experience in this market will be willing to answer. 

1. I read that property management companies charge near 30% for their services. I feel like this is essential for the success of this type of rental. What are the signs of a good management company?

2. Am I correct in assuming that if I purchase an established property with a documented history that my management company can maintain this from a marketing standpoint?  Is this the right move for someone new to this rental type?

3.  I also read that there are numerous additional maintenance requirements for cabins such as regular staining. How much reserve cash should a person keep for this type of rental? (I am planning 50k)

4.  How do I find the right realtor for cabins?  What type of downpayment and financing can I expect for a cabin with a history of profitability?

5. Assuming covid will not be our final pandemic, were you offered assistance when the city was shut down?  How did you survive?  What would you have done differently?

6.  Lastly, if you've had this type of property, what do you wish you would have known ahead of time?  Would you buy another one?