Thanks to COVID, for a couple of years, you can actually make enough money to be cash flow positive even if you hire a property manager AND have mortgage payments. 

I have a list of them that I can share with you.Chicago, without a doubt, has some downsides, but there are also a lot of positives, like the inventory of older multi-family properties and price points at all levels.Investing out-state can be challenging because of the distance and the need for boots on the ground that you can trust 100%.

Additionally, the price point is still cheap enough to find the 1% rule and positive cash flow and there's amazing appreciation potential.

My questions are what books or other resources would you recommend to someone just getting started and also what is the best path to get started on in real estate for someone in my position?

The positive is you can get them out with 60 day notice so 60 day escrow would allow the unit to be delivered vacant (assuming zero issues terminating the rental)good luck 

You’re in a great position with a property that’s appreciated significantly, a low-interest mortgage, and clear goals to boost cash flow and transition into full-time investing.

On the positive side, it seems like you have a good potential BRRRR that you can use to purchase additional properties.

The Suburban markets with New construction offering decent builder buy-down rates 5s %, and selling completed inventory homes to investors is an opportunity we’re pointing investors to, as well as Duplexes outside the city, that’s where we’re finding some of the best options to get closest to positive cashflow with 20/25% down.

I wouldn’t come up and say I am new in the business but if someone ask me I’ll be honest, that may work for some, but not others, it who cares anyways, you won’t get everyone, you want those that will want to do business with you.I will also reiterate that even if you are brand new and some ask you, turn around to a positive, if they say “but so and so has been in the business 20 years and have done many transactions blah blah blah” you can turn it around “you know mr and mrs seller, that is a great agent with a great track record, but don’t mind my asking, they are doing so many deals a month and so and so a year, how much time do you think they would dedicate to your home?”

If you rented this home and it was putting $3K positive cashflow yearly in your pocket, the returns would be 3/4=7%.