Talking to my agent, who has three of his own short term rentals in the area, tells me, my calculations are ultra conservative and the numbers do add up for this area.

It’ll be hard to delegate landlord responsibilities but if you have someone that can do it, pay them well.

I would appreciate any tips/advice/books that you can provide me to help jumpstart my real estate journey!

Worst case, structural and roof repairs.If it is in the worst case side I might not tackle a project like that in that location due to the added complexities.Once again thank you all for your responses

Any tips appreciated

Thank you all again for the variety of responses here.

Thanks Sarah and everyone for the response!

You want an accountant who can help you strategize and who is responsive when you want to know the tax consequences of the decisions you are making throughout the year.Good luck in your search.

In my leases with homes, it is the tenant's responsibility and I make that clear at the showing before leases are signed. 

I'm not sure what exactly you're looking for in a real estate agent, but she's very responsive, gets offers written up and sent out fast, and will remind me to think about certain factors regarding the area/property when I get off-track.