While they are very nice and I believe good people, I have had a few deals fall through after months of hard work on them because they do not fight for the deal in my opinion. 

Some leases are written with 60-day notices, etc., so read the lease as it could trump the statute.

Then decorate the place up, nice lighting, signs, etc.Then you can move the needle. 

Nice weather.

And make sure the floors have a nice contrast such as the middle ground flooring you touched on.

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

I was trying to be nice and told him I need to think about it. 

Perhaps thinking of a  modular style home to get it up and running quickly.

You can still find some great cottage style homes or even 2-4 units close to the beach that have great STR returns.One good thing about being out of state in IL is you can find a good Single family home, Condo, or Townhome and call it a Vacation home and only need 10% down. 

Hello BP community:I am under contract on some land that I am considering building multifamily on.It appears I can build approximately 80 units on the land (based on permitted density), which could be more or less units depending on the exact style of units we would construct (one or two story, etc).