Borrowing against your paid off house without an income puts way too much pressure on the success of whatever deal/project you decide to pursue. 

No one will care more about your success then you.

I think STR Insurance successfully drew many misunderstood pictures that regular insurance will not cover guest’s damage to the house.

If you can come in and operate effectively I think you'll find success rather quickly due to that.BTW - for a property management platform I would highly recommend Buildium.

Your team is key to your flipping success. 

@Emily Gowen so as you pointed out you would not have to do a 1031 exchange on your current home to avoid the capital gains tax and coupled with what Dave Foster pointed out I think, speaking from experience you would have a high likelihood of success. 

I’ve worked with several first-time investors, including out-of-state buyers like yourself, and it’s 100% possible to build a successful short-term rental (STR) business even when you’re managing remotely.

With the growth mindset you clearly have, you're building a solid foundation for success.

Most of our out of state investors in Pittsburgh find success depending on their expectations.

The better your can run and manage that business the successful you will be.