I ran some very basic numbers on option 1 and if you can get a ST/MT rental per your comments and other assumptions you list, this could be a deal for you.

Homeowners will always pay more than investors, and the easiest way to get the property in front of the masses fast is to list it. 

For example, you could showcase the family-friendly amenities, outdoor spaces, and stylish interiors all at once, similar to the one shared here (this is a listing photo, so I would recommend you change the text to fit your guests).

The energy in person is different for me, and I've made some of my best connections and friends at Chicago meetups.Here is a list of the Chicago event from BP: https://www.biggerpockets.com/forums/521-real-estate-events-...I also have a list of ALL THE CHICAGO MEETUPS that I am happy to share with you. 

Those are some very different markets you listed.

Have 3 loans to refinance in the next few years and DSCR's are added to the option list.

they're better off just listing on the MLS.  

It may not be a bad idea to also be added to a MLS search to receive any new build listings. 

One of the challenges of beginning wholesalers is they do not have a buyer's list.

Do negotiation with the tenantIf it is item 2, what are the do’s and don’ts