That method will increase your ROE significantly more.Also read the BP book on BRRRR investing.

Find Brandon's videos on YouTube for the "four square" method of analyzing homes and practice.

Here are some thoughts I hope help.The benefit of selling now is that as an inherited property you will likely pay no taxes because you inherit it at a stepped-up basis.I'm not a huge fan of buying a house that has lot rent.

Find Brandon's videos on YouTube for the "four square" method of analyzing homes and practice.

I’ve been diving into real estate and learning every step of the way.

Congratulations on starting your real estate investing journey—that’s such an exciting step!

Any suggestions on where I should take my next step in the right direction. 

Finding handymen is NEVER easy:( Often, you have to use trial & error method and weed through several before finding one that is acceptably (never pefect) reliable, quality, will fix warranty issues and has decent prices.Try visiting a Home Depot 6-8am on a Saturday.

I’m working toward my first deal now, and your story reminds me that success starts with stepping into the unknown.

I feel I have a rough idea, which is..I'm in Rogers Park, my next important step is to wait out 1.5 years until I can fully rent out the condo, but for the meanwhile get a roommate to save more money.