It works if you buy low enough compared to the properties market value. 

The larger landlords have a lot less movement possibility (often times a take it or leave it) versus the small town landlord. 

Hi @Michael Cutting, great questions and it sounds like you have a potentially exciting opportunity.I am going to have a slightly different opinion compared to @Rob Beland.I agree about being able to require them to sign leases.  

The challenge @ this price point is the variation between the low comparables & the high comparables.  

Assuming your land is as-of-right or approved for the project you are going to develop, you will then need to think about construction costs, soft costs, and financing costs, revenue your project will generate and compare that to the market.

I've never done it before but for a starting point figure out what the investor's minimum rate of return (how it compares to a bank, CD, or stocks).

If anything, this will allow you to compare your mortgage person to his/her.

This allows you to compare to other investments.  

The key is to get them at a discount compared to a single family home to cover the expense and hassle of dealing with the hoa.

What you will likely want to do is compare comps and decide if it's worth actually buying.Assuming you will buy it because you've lived in there without knowing what the price per square foot will be is a bad assumption.