If the property that you are considering is not in good shape then you must get it at a price that allows you to put it in good condition immediately. 

Additionally, might check local laws concerning costs a tenant is required to pay for to obtain a lease.However, you can have problems saying an additional insured, I see the trend of PMs trying to horn in on liability coverage, I suggest you speak to the agent involved.

http://www.fastcoexist.com/3049280/this-shape-shif...How cool is this?!

Good for you, it seems you try to keep your rentals in good shape... just be emotionally prepared for someone to trash the place :) You should be able to attract good tenants with a nicer place!

The magazine noted the trend among younger people is to rent rather than to buy.

I have a brand new 4plex I house hack and I am most concerned about keeping it and the neighborhood in tip top shape.

@James L. yeah, maybe we'll start a "Build & Hold trend here on BP!

I believe that New York is ahead of Chicago on housing trends and I'd like to visit and actually tour similar properties in NYC to get ideas for how to market my property (small square footage, making the most of the space, creative ideas for maximizing usability, etc.).

It sounds like You've already expended the money to keep them in pretty good shape for a number of years. 

Any trends you're seeing?