One of them is a good friend of mine and the other one is a young lady who works at the hospital and says “I’m just looking for a bed”, and honestly imaging she's going to be super quite and practically not even there... but I am curious as to how to determine who would be the better tenant, while also not being a greedy piece of 💩...I want to help them both, but also trying to be a savvy businessman, I don't know what the right answer is? 

Contractors are very hard to find, move extremely slow, and are increadibly hard to trust.

Looking for a good general contractor to build a guesthouse on our back lot. Any recommendations?

I'm going to be honest, I don't trust anyone.

If you guys could help me that would be extremely appreciated.

Some cities are going to the extreme though.

But if you are handling this as a flip, just putting it in a list...Upgrades to the house since its purchase on August 2018:  paint living room, paint master bathroom, new kitchen counter, terracing yard with retaining walls, planting XX bushes and plants, adding drains to basement and yard, replacing living room lights, …The idea is to honestly market the house, identify the work, but do not focus on it. 

I was able to give cash for keys and then pay the bene off.. he was an attorney so it was a little easier dealing with him.. the owner or people losing it were full blown tweakers and hoarders extreme..

To be honest when things get a little bit overwhelming for me, I go buy another house..somehow it recharges me and gets me excited again.

Make sure they are not bigger and stronger than you.. or pay them extremely well.