Hi @Jacob Dalton,Thanks for sharing your situation—it’s clear you’ve put a lot of thought into this decision, and I can understand why you’re concerned given the challenges of being a landlord in Cook County.Screening tenants is definitely a key step, but I agree it’s not foolproof.

Probably going to be a check.Smart contractors are starting to understand that convenience matters to customers and being able to take different methods of payment can help them collect their money.

IMHO the key is having an agent on the buy side who understands the process and can make some magic happen for you. 

I’m struggling to understand why all of this is necessary just to use their property management software.

You don't need to know everything to get started; you need a foundation to build on, and the rest will come through experience and then refining your education.You can build a basic understanding of investing in 3-6 months.

Those types of things can throw curve balls but in my opinion, at the end of the day it wouldnt be worth much without friends and family and I understand his loss.  

They don't understand how to price effectively, study the market, set boundaries with tenants, establish policies and procedures, communicate, and dozens of other things.

The first thing to focus on is understanding your target guests and tailoring your property to their needs.

For context I am a full time lender and understand DTI and have very good credit. 

We're new to real estate and would appreciate advice on our current home in Texas and our future place in Oregon.We love our house in Austin and aren't ready to sell, but as a long-term rental, it would yield (from what I understand) negative cash flow, covering principal and interest but not taxes and insurance.