Retirement with short term rentals??? How would you get there.?

[Brandon Stevens]

For people in this space, or in RE investing in general..how would you answer this question...

A couple wants to retire in 5 years, they would like to use short term rentals to supply them with 60-80k a year to live on. They have 300k they can begin investing with.....can they get there? 

They would be happy to live in the rentals in the off season if needed to facilitate the plan and Ideally would like to own a lake house, house by the ocean (in town), and a home in their midwest city. 

If not, would bringing another couple in with a similar nest egg be able to make it happen or would simply more money upfront be needed?

What are your thoughts, I didn't have an answer for them other than well most vacation rentals I think are considered a success if they just pay for themselves..... :) but maybe there is a strategy out there...