Jesi, I just traveled to Maui for the first time in early January, it is so beautiful.

I am torn because I also like to travel, fish, backpack and making money takes some time. 

I have yet to do a 1031 exchange or a cost segregation study (I'd like to see how this plays out long term when selling or doing a 1031 exchange into a different property) or expense business travel/mastermind/classes. 

It is also worth noting that property management is often closer to 30% of gross rent for a short-term rental due to the much more intensive hands-on management compared to a typical 10% for long-term and as such, I agree with recommendations above that medium term rentals may provide the best of both worlds if you are able to tailor proximity to a local need, e.g. hospitals and travel nurses.Again, happy to relay my personal experiences in the area if you're interested.Best of luck,Patrick

•Downtown Orlando offers a different rental audience—primarily business travelers, medical professionals, and convention attendees.

They do seem to need rentals around that area for hospital visitors, maybe traveling nurses, etc. 

I have lived in Hawaii for many years but now that I’m a traveling healthcare provider, I am off island more often than not.When I’m not on contract I would love to have a place to return to and when I’m away I would love to rent it out for some additional income.

Many of my customers who are traveling nurses buy condos or townhomes in Florida as vacation homes, then rent them out when they're not in town.This system has proven to be very lucrative, as it allows them to service the mortgage debt and generate a good cash flow.

The Expenses is not important here but for me, it's convenient because it is part of the travel and work we did in the property.

We are from there originally and travel to the area to see family and the explosion of the number of people traveling to the Hocking Hills has made it the 3rd most visited place in the state of Ohio behind Cedar Point, Kings Island.