I understand and have high value on flow, texture, space, color, end user/consumer, and general aesthetic.

While you should care about the shingles (the material responsible for the aesthetics and main wear of the roof), the other materials are likely pretty comparable and the skill of the roofer is going to be much more important than the actual brand of materials used.

The more savvy investor or better STR marketing investor can make inroads in raising that nightly price point by upping the aesthetic game of the STRs.

The other units that I have seen in the area were similar in size, age and amenities…they were just overall more aesthetically pleasing, slightly more updated and cleaner.These units are 2/1 but still on the smaller side and super dated.

If you allow your tenants to maintain their lots like a garbage dump in the name of personal aesthetics you own a trailer park.

If not, a frosted, operable, vinyl window would be preferable to glass block with a small vent opening for reduction of humidity and aesthetics.  

Can't comment on the location or the aesthetics.

This will serve as an incentive to him to help you in any way possible to find a qualified tenant such as:- allowing you to show the place multiple times when you have a good prospect AND keep it neat and tidy so it is aesthetically appealing.

You will still gain appreciation in Streamwood and if you price the rental amount of the home within what the area can sustain and spend a few extra bucks to make the home aesthetically appealing and have the most up to date fixtures and finishes, you will rent with better cash flow than Schaumburg and with the same market times.  

I do however recognize that it's easy to say "replace the 3 tiles" with no idea as to what condition the place is in (or any of the other aesthetics).