In Oak Park, we have had people like Ray Kroc, Ernest Hemingway, Bob Newhart, Sam Gianncana, Betty White. 

But wanted to ask here what other people have done or if you have any ideas.

I appreciate you listing the steps you took / people you went to in order to fill the gaps.

Most people assume that house hacking means living in a 2 bedroom 1 bath duplex.

I am looking for advice from people who have done this in the past.

If enough people reach out, eventually it would be great to start a meetup group for STR investors in the area.

Then I work with a local insurance broker give them a valuation of the property, explain that the property is being rented and by how many people.

Quote from @Chris Seveney: @Charlene Kingsnorth have you had an sec attorney also review what you are doing as if you're are having multiple people as part of a loan participating in it depending on the state this could get you in hot water - so be careful  good point Chris some state allow fractionalized deed of Trust mortgages other do not or require PPM like documents prior to offering them..

The best way to start is by surrounding yourself with people who are already doing what you’re trying to do.

Quote from @Vince Scipione: Yes, they are a popular choice where I live and work, however with the ever fluctuating cost of oil heat, many people have swapped over their boilers/furnaces to what is called a "Propane Gun" essentially it is a device that is affixed to the front of the furnace/boiler that injects the propane and ignites it.