I’m about to be at the 3 month mark prior to their renewal and want to present a new lease.

Would there be any problem if I sign a purchase contract prior to the house going through probate?

Yeah the nearest comparable town is roughly 1 1/2 hours away.

Compared to A 90-100,000 loan to fund the down payment and the rehab.

@Corby Goade it would cost approximately $60,000 to build a comparable unit.

I lived in Toronto and Montreal prior to moving to the US about 30 years ago.

A lot of the newer 4-Plex in areas such as the Medical Center come with higher Purchase prices compared to the Rental Income.  

How is the weather compared to Maui, and what kind of net income can you expect per year on a small 500ish sq ft one bedroom that's oceanview/front?

Understand the fees involved and calculate the total cost for an entire year of management so you can compare the different managers.

When the total number of jobs is 637,000, this is only a small drop in the bucket, but it is a positive sign that you would look for in a market.If you create a spreadsheet like the one above yourself, you can literally put in any data points that matter most to you and compare from there.