To simplify the existing lease I thought about asking the tenant if they would be ok modifying the addendums to get rid of the resident benefit package and the building protection plan. 

Initially we did a light renovation on the rental unit and a larger renovation on the 1st floor.

Chicago, with its vibrant neighborhoods and strong rental market, is a prime location for this strategy.

.: Quote from @Andres Murillo: Quote from @Pearse Cafiero: Hi Everyone, Trying to figure out the best way to go about getting my first rental property.

For example, I can't see a way to use any marketing packages??? 

The BRRRR method (Buy, Rehab, Rent, Refinance, Repeat) could also be a great strategy to recycle your capital.To find deals, try direct mail campaigns targeting absentee owners or distressed properties, or go driving for dollars in neighborhoods with strong rental potential.

Can you set up an account and post a rental directly on Zillow if you are not a realtor? 

@Rosette PooleRecommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

I use a CPA, too, but I like to do my own bookkeeping throughout the year and send him a tax package quarterly to review.  

I like the feeling of being close by to my rentals and managaging myself.