I used to live in northern Illinois, so close to Wisconsin - there are several smaller towns around lakes that would be good for short term rentals. 

The population has been growing here year over year over the last decade, it is home to The Ohio State University which has over 50,000 students that live here along with those that visit, and it also holds a diverse range of young professionals and traveling nurses to fill the demand of the multiple business corporations and hospitals stationed here.

We moved to Florida a year later and rented out the house fully furnished from July-December to a family who just needed a short term place to live.

I have lived in and owned property in Tobin Hill over the last 9.5 years. 

Let her know that it is only for her to live in and if she has guests that stay for more than 2 days (or whatever you think is reasonable) in a 6 month period, she needs your permission....or she has to find another place to live. 

I have been living in a duplex househack that I purchased in 2021.

We are looking to buy a 5 bedroom+ home that we can convert to 2 or more units where we live in one unit.

Last, if anyone lives on Maui and would like to connect I am always looking for like minded individuals to network with, and maybe, do some deals with! 

You may drastically lower your living expenditures and increase your capacity to save for future investments by renting out some of your units while you live in others.Starting with a duplex or triplex is a sensible choice, given your aims and money.

I am currently living in the Bay Area, California.