I’m trying to redo my floors because they are outdated but the hardwood is in good condition just want to refinish them a different color.

Or a dab of caulk and color match paint to the brick and you'd never notice it unless you looked for it.Is the outlet installed in brick or drywall?

I use a filler that is the same color as the paint often I fix the holes and no need to paint over.

I believe they make a color close to the hardwood floor you currently have.  

@Ashish Acharya thanks for the color!

We painted it to match the neutral wall color used to paint the rest of the house.

That being said, one tip I can give new investors and out of state investors is to have at least some sort of grasp on the neighborhoods to invest in before just diving into making offers and such.With Chicago being such a large city filled with a ton of vibrant neighborhoods, I don't believe that it should be up to you as a first time investor or out of state investor to learn about these neighborhoods through your own research.

The only time I've seen this turn into an issue is if you offer to pay for the flooring and then the tenant comes up with more requests every couple of months (e.g. new toilet, different color paint, new washer/dryer, etc.) 

I love the idea for the lighter colors, do you think the SW agreeable gray with white trim will be good?

I gave too much control up without having worked with this guy before, and several aspects of the construction work went off course, including the kitchen design and color pallette.