Background: My wife and I live in San Jose, California, where we are renting a basement apartment from family for a great discount.

Inventory is so low in Milwaukee, that sellers don't need to give much of a discount.

I'm just saying anyone who has a solid value add strategy that can be repeated over and over like buying and selling new trailers like this is an example of a strategy. but buying discount houses without rehab knowledge for out of state investors is risky 

But I also have many 2/1s attached to studios where I make the 2/1 pay the entire bill and their rent is discounted 100$ to market which usually ends up in them profiting a bit monthly.

If you can buy it a discount might be worth considering. 

This is exactly what I want to do next and it helps tremendously to hear success stories!!! 

I personally run a Professional Landlord business to manage our own properties and others for a significant discount compared to traditional property managers!

If this property has big defects you should command a discounted price.

In my case, I'm following all the rules of a rental property, along with taxes and fees, but I am giving them a slight discount.  

Off-market deals usually come with discounted prices, no bidding war, and less pressure.