MJ looking to invest in Chicago market - 1st time!!

[Matt Jordan]

What's up BP,

I am officially looking to make my first rental purchase in Chicago hopefully in the next 2 - 6 months. I currently own a 3 bd/1.5br home in St. Charles that I've lived at for 3 years. I am looking in Chicago along the loop, bucktown, lincoln park area. I have a few hurdles I am trying to figure out to complete my master plan:

First of all I am unsure of what I am looking to purchase; 2 bed/1bed/studio/4 unit? Should I take a 15/30 year? Should I refinance my current house that is at 4.25% and use equity to use towards the rental? Do I buy an outdated condo and put 20-30k into it to increase the rental income? 

The plan is to buy a studio/1 bed and throw it up on Airbnb. I would hopefully rent it out 50-75% of the time and charge surge prices on events/concerts/conferences. I know it's about to be the winter so I am unsure of how often the unit would rent out.

I would need to make sure the HOA allows rentals and that there is no rental cap or restrictions. In case anything happens with Airbnb with restrictions it would be nice to have a plan B. This is also a potential unit that I would live at down the road, or if everything goes right the plan is to slowly buy units and throw them up on Airbnb around the country.

I have around 40 - 70k in cash to play with + equity on my current house.

Any and all advice is greatly appreciated!!