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..

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

One other thing that people in their 60s can consider is - if you are planning on taking Social Security and making passive income part of what you live on, rental income may not count as income against your Social Security benefits.

Also Mid-Term Rentals to traveling professionals, people displaced for insurance reasons, or doing a renovation to their home and needing a place to live for  3 months or more are also possibilities.

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.

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.

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.

It is an amazing city with great people and plenty of opportunities in the real estate space.