In going through MLS listings I was seeing multiple duplexes and triplexes for 100-300k, and most of them seem very undesirable!

That being said, life DOES happen, and to have no way to redemption after life has taken a wrong turn (think divorce, catastrophic accident, cancer, etc) is unconscionable, in my book.I see that you have an engineering and finance degree....surely you are not making an argument that everyone who graduates with debt is "unqualified" academically, or with an "undesirable" course of study?

Take an RE course so you feel like your doing something for yourself to make you happy and gradually move away from the undesired job. 

I would post warnings in writing to correct the undesirable actions.  

Maybe lowering the rent doesn’t allow you to take care of the property as well as you should and therefore attracts undesirable tenants while pushing away those you would like.I believe capitalism always works and the market will dictate the rents.

Seems to me like a good market to invest in for the most part I am just trying to see is there anything that make it undesirable for people to invest there.Ive found some midwest cities have interesting tenant laws such as Chicago that make investing a little more of a hassle than others.

It certainly makes it easier to replace boards, but seasonal gap changes as a result of humidity may prove undesirable.  

As such, he wanted to know if what he was doing was legal so as to have a gain some leverage should this guy continue to give him undesired drama and bs.

However, I’m unsure how to finance this for a few reasons: A) I only have $90k max to put down, B) if I acquired a hard money loan, the sale of one parcel would still leave me with 200k left on undesirable loan conditions.

Other boards want to create huge war chests to have the best of everything, and further use a hefty HOA fee as a way of keeping 'undesirables' out of their complexes.