Every tax season, I see people unintentionally overpaying the IRS.

Most people looking to hire on there are looking for cheap bookkeeping.

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.

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

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

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

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.

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.

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