I am a travel nurse practitioner so I was considering taking an assignment in Dallas in January to go ahead and generate income there.

That could be an up and coming community for those that travel into Indy or up to Lafayette. 

Once you househack your own property, I’m pretty sure you’ll be confident to proceed with other ways of real estate investing.Hope this helps!

Make sure the sign off is done before closing then feel confident in going ahead with the project.

Be confident with the market research and due diligence before making offers.

Right now its via Travelers, but your broker should be able to shop it for you. 

I am fairly confident you will be able to find a company willing to manage.

No - Chesky is wishful thinking. a) Most people are not nomadic in nature b) It takes a lot of money to travel and stay at Vacation Rentals (the cost of the rental, food, auto and gas, etc.)For most people, STR trips will continue to be a nice little getaway alternative to traditional hotels....although I believe their usage will grow a good bit anyway.

Based on my experience, I would avoid MetLife and Travelers and a little unknown company called Maison Insurance. 

However, it allows you to get in the game and gain confidence to do bigger and better things, which you have already started to do.