Make sure everything has been updated to modern standards or you're in for a nightmare. 

If I put $15,000 of rehab into each unit, installing modern rental-grade cabinets, granite countertops, nice laminate flooring, stainless steel appliances, modern light fixtures, new plumbing fixtures, etc., is that worth getting $250 extra rents per unit?

And I want everything to look and feel modernized.

I mean, if the tornado hits they're typically going to pay "replacement value" which would yield a smooth driveway, modern plumbing, and a new water heater.  

I want to rebuild a detached garage on a property in Kent and the city is telling me i have to stay exactly on the same small footprint as the existing structure - which would be grandfathered - if I get off the footprint I would no longer meet modern zoning requirements for set back.

BTW, I lived not far from Naperville in Westmont and can tell you that the housing stock in your area presents no shortages of opportunities as there are so many old homes in great locations near Metra stations that need to be renovated and will sell for top dollar once they have a modern floor plan and nice finishes.  

I am an oddball in modern day because I have all of my staff that actually works in my office and I do not currently use a virtual assistant. 

I would like to do about $300,000 in improvements over the next 3 years, starting with curb appeal and energy efficiency items, and updating units to modern B- grade as they turn over.

Payment standard $1651 (the amount generally needed to meet modernly priced dwelling based on the number of bedrooms) 4.

Soon to be demoed and remodeled to a newer, more modern and functional kitchen.