Answers to the other questions depend on a lot of factors, and the temperature of the market as we head into presumably tough times. 

I have a job that also affords me a lot of spare time in my schedule and I'm looking to use that time to begin/continue/grow a real estate portfolio.

Hello! My name is Abriauna. I have been listening to Bigger Pockets podcast for a couple of months now and I am learning so much but still in the beginning stages of learning how to jump in to real estate investing. I...

.✅ Stronger Tenant Relationships – Being involved directly allows you to build rapport with your tenants, which can lead to better communication and longer leases.Cons of Self-Managing❌ Time-Consuming – Dealing with maintenance requests, late-night emergencies, and tenant disputes can quickly become a second job.❌ Legal Risks – Chicago has strict landlord-tenant laws.

We have several different people lined up to clean ours depending on time of day and how much lead time we have.

Be very careful with this as a first time project! 

@Michael Baum how many Short-term rentals do you manage this way where you are on call all the time?

if you're W2 and full-time, hourly or salary, you should be able to go off your pay stubs for qualifying.

I find that most of the time, paying points up front isn't worth it in the end.

I have from time to time spoken with the city administrator, economic developer, & a person at building planning commission.