For background I recently purchased a 5bd/2ba in Denver which I plan to live in myself (got a 5% down no PMI HomeReady loan for it)  as well as rent out the remaining 4 bds by the room.

All the background work that is done to be even able to start a job takes time, patience, intelligence, hard work ethic, relationship building, trustworthiness, etc.

Let's say you did a Credit Check which was not good, but the tenant claims it's from an event like a divorce or student loans or a hack.The next thing I do is an Eviction and Criminal Background check and a Bank Statement Check to make sure that the prospective tenant is not pulling the wool over my eyes.Imagine that the prospective tenant has a rap sheet pages long and you decided that he looked honest enough and let him in.There are so many horror stories of bad tenants and yet I see posting from new Landlords all the time skipping a FULL due diligence Again and Again!

Some of the more specialized areas might but most folks in this field come to it with other backgrounds. 

I would then seek out a competent attorney that has a background working with real estate investors (one with specific knowledge of wholesaling or assignment of contracts and the marketing of such).

I am assuming because I have no construction or engineering background yet, or maybe I am taking the wrong approach.

Without knowing anything about your background, that's a difficult question to answer.

He has a very good job and great credit but is young and immature so I kind of just want him to go away BUT hate the hassle of having to show the place again (40+ min drive from my house each way), run background checks, etc.What would you do in a situation like this?

Hello @Duane Smith I was previously licensed Series 7 & 66, Life & Health so you have a great background in terms of knowing what is required.

Background: We live and work at an all boys boarding school.