I would have an extra light on a stand to brighten the spaces.2) Your first photo is of an empty room to a doorway.

They'll likely have follow up questions about who handles maintenance, larger SD, etc... so be prepared to quickly answer these.Value to mention:- Professionally cleaned property after each stay and exterior upkeep- Staged photos that you can share with the owner for marketing purposes- Capex coverage up to $XX,000 (might need to include in SD)- Extra $XXX per month (likely may need to pay a little extra in rent to make it worthwhile, otherwise they can collect the same amount as LTR)Also, google "Airbnb apartments" or check their website. 

If you are still willing to stay in the same unit as your brother you can get a 2-4 unit building, rent out the other units and still rent a bedroom within your unit to your brother for extra income.

In practice, this could mean 5 extra days that no rent is collected.  

The difference between MKE and Chicagoland does not warrant the extra effort that comes with going remote.Everything gets so much more complicated as soon as you can't swing by your property after work.

Make sure it can handle the extra capacity before you get too far along.

We kept extra bags in the bottom of the can under the current trash bag.

A neat feature with xfinity (no I don’t work there 😀) is the voice remote and once you have one box you can stream the service to the rest of your TVs cutting down the cost of extra cable drops. 

I do not see a need for extra cost or tech not all of your guests will appreciate (i.e. older generations).

However, you appear to be the type that doesnt really want to deal with some of the work or extra effort needed for those strategies.