First time home buyer in Chicago

[Tom Horwitz]

Hey everyone! I’m a 26 year old first time home buyer in Chicago who has been actively looking (have an agent, pre-approved, etc). I have roughly $85,000 liquid and plan to purchase a condo in a desirable area of the city (lake view/Logan square area). My plan is to put 20% down on a property between $250,000-$275,000, live in it for a couple of years, rent it out with positive cash flow, and repeat the process.

If you were in my position, what would you do?

Look forward to connecting with you all and appreciate your feedback, thanks!