Your 1.2-1.4m new multifamily may only generate 8k in rent tops.

A friend of my wife’s brother in Maui has a 5th generation cork and cattle farm near Gibraltar, Spain.  

Also you mention he has an awful reputation yet you acknowledged in your initial post you repeatedly buy properties his brokerage represents...not quite adding up.

Initially, this might seem like a great idea as you can maximize rental income by renting out bedrooms kind of like college student rentals.

Hey John - I appreciate your initial reply.

We are looking for 3 year lease if that is acceptable with you.My initial reaction was to decline this offer.

We have a software called EZCare which our cleaners will take post clean pics and it generates a report. 

The initial thought is you are probably charging too much if no one is interested, or your photos or description are bad.Four beds and only one bath probably reduces demand as well, that’s potentially a lot of people sharing one toilet.And it is winter - I’m in Buffalo, I hate listing rentals this time of year.

We are literally next to a golf course and about 10 mins from a ski place and I don't think fancier amenities would generate a ton of ROI. 

You are right about the risk that comes with the holding period but in my opinion sometimes you have to take the risk and make sure the profit that you generate is higher than the costs that you paid by holding the deal for a specific amount of time.