I prefer to operate my business independently.

Having family in the market is helpful because you can get an independent set of eyes on the property. 

Below are the antonyms for freedom, according to Roget’s 21st Century Thesaurus:Dependence and captivity… According to this definition, freedom is some sort of independence from some external force or power.

This is not stopping me from pursuing my dream of financial independence. 

You need to connect with an independent insurance agent that specializes in investment properties. 

Do the research on Air Dna or even just AirBnB ... lots of ways to get in. Depends

I read Set For Life by Scott Trench and knew that House Hacking needed to be the first step to financial independence (Especially here in the Boston area where housing is so expensive!).

., new roof from last year starts leaking and the contractor is out of business)If you have a solid Independent Contractor (IC) agreement in place, you can push all of these risks back on the contractor's insurance program. 

I own some properties independently.

There is also an option to have a contractor come assess your house and let you know what you're eligible for, but that's $50 and I think they're independent (energy star certified???)