You have the right things to analyze here, but STR might be a tall order to do arbitrage unless you have the funds to go heavy on the furnishings.

There are tons of great groups here in Chicago. 

I'm in no way affiliated with this company but here's a link that may come in use should you need any additional forms in the future @Morgan McRaehttps://www.firsttuesday.us/in...

I've been at 100% occupancy for my small spaces for the past 5 years.My only feedback is that $2 per month per sq ft NNN seems really high to me, but each market is different. 

The reason to do so is not necessarily to reduce cost but to be efficient.

You are asking me to extinguish any leverage I have and left vulnerable for anyone to steal the deal from under me". 

Admins @Rene Hosman, is there any way to go back and delete all of the downright dangerous advice he gave to beginners over the years on here so that the forum archives aren't full of BS? 

One of the lease for a rental is about to expire and would like to change from single family to rent by the room and try, to market for regular leasing we normally go to Zillow and advertise for free, but for rent by the room not sure which of all the sites out there will be the best option(s), some of them are for free, majority pay a monthly or anual subscription ($99 to $200).Do you have any guidance on which to select?

2) What would be best way to market those rooming houses.

We will allow you to use a new employment contract as qualifying income 6-12 months prior to your start date.