Not enough current income to move the needle, but all the knowledge required to learn and, if you're self-managing, the always-present "the tenant could move/break/have problem any minute of the day" possibility. 

On the tax side, I would encourage you to partner with a knowledgeable real estate CPA who can guide you through the transaction to ensure you can meet the qualifications of the STR loophole.

I really do appreciate all of the comments folks have made and it’s clear that they have systems in place and I hope that knowledge will aid me in my endeavor. 

If you are trying to piece everything together yourself remotely I think the time and brain damage and extra cost in time and cash you would be better to go yourself and do it. 

You should know from your own knowledge of the area and the property whether it's a good deal or not. 

In addition, you can listen to the Straight Up Chicago Investor for great local knowledge and contacts. 

Had the ability, experience, and knowledge to succeed4.

Mine is to network and also to gain knowledge.

I know this is an old thread but I wanted to see if you were able to get more knowledge on this basement conversion and what you ultimately decided?

I am certain we can share knowledge and resources.