Expertise and Experience: Property managers have specialized knowledge in managing properties, including understanding local market trends, legal requirements, and tenant relations.

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. 

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

I know this because I was once a victim of exactly this, so my knowledge is via experience.

I'd recommend being very careful about how involved you get with college kids and the choices, decisions and responsibilities that they need to make for your property. 

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.

These are all people who, if given a choice, would rather keep their house than sell it.So, what’s happening?