In regards to pure vacation rental I don’t have experience but I run small 1bd airbnb STRs in my city that targets travelers and workers - not really vacationers.

Sometimes part of Oct for cyclists and Thanksgiving once.I have an inquiry from someone who is traveling for work.

If we have a STR rental in Florida which we rent from Memorial Day until October, then travel to our STR in Brasil & live there from October until May, would the travel be deductible? 

I have recently been given an opportunity to enter a sales training program that would last a year and require travel all over the country.

My husband and I have been talking for a while about ways to increase our cashflow so we can retire early and travel the world together.

That being said, the biggest question is whether that time could be better spent doing something more productive (finding & evaluating other deals, etc) or more enjoyable (spending time with family & friends, travel, so on). 

This is definitely a home that families would want to vacation at but I am concerned about people traveling less due to covid and seasonal fluctuations in occupancy, paying the cleaning lady every time someone leaves, and the extra time I’ll have to put in to manage the property.

They charge something like 40% of whatever is recovered.So....small claims court, for a landlord in a different state, will cost you more in travel and time than you will ever actually get back in your pocket.

You can Airbnb one unit, you could medium-term rent the other (still furnish but rent for 3 months to say traveling nurses or business people).

I know hospitals often have traveling staff, and that medical schools often provide housing for students placed in teaching hospitals.