I have been volunteering with local Habitat for Humanity groups to learn how to renovate houses, and currently looking for my first house hack or flip in the southeastern MA area (have been looking at areas such as Barnstable, Plymouth, and Bristol counties). 

You'll naturally meet  people who want to get rid of their headache, I mean house, that they inherited. 

My thought is any tree on the property could at any time fall on the house, we have two other large trees in the yard as well.

I found a really solid duplex opportunity to house hack but the property has existing leases through December of 2024.I am looking to buy and move into a property in the next 2-3 months. 

I buy properties from turnkey companies and also from the MLS and give it to PM folks.Lately I am noticing that in the houses that I have purchased there are issues that have surfaced which could have been handled in a better way when the property was bought itself.

Here's a fundamental explanation to get your juices flowing:Assume a house costs $200,000 and rents for $1,500.

So it's a one stop shop kind of deal and with everything being handled in house the interests have to be mutually aligned because that provider is married to you for the longevity of the investment. 

If the property is worth more with the house then without.

I know I'm not bound by Fair Housing Laws with only 1 property, but it's something I want to be conscious of as I develop my process both for this go around and in the future.

If you are trying to convert a property under and hoa into an str, your job gets even more complicated as the HOA itself may have its own regulations IF it even accepts it at all.caution: STR market is over saturated in these parts and some of them are shuting down and being converted into corporate housing, mid term rentals, or furnished long term rentals.