(End)Unfortunately, HOAs are often ran by individuals who are not the most knowledgeable on regulations, accounting practices, and more - and property managers do not want to intervene for fear of losing the contract. 

The fact that they knew about this and didn't tell you up front says to me they were hoping you didn't actually run reports. 2) Be sure to know the regulations in your jurisdiction.

Also check if there are any boarding house regulations in your area that would impact you. 

I will be doing my own research on local laws & regulations, but want to do this 100% by the books.

The first thing here would be the regulations and laws governing acquiring properties, managing properties and selling properties.

.❌ Legal Risks – Chicago has strict landlord-tenant laws.

It looks like there's quite a few regulations in place at least in Nashville, IN (not sure about Bloomington).

I know that i could buy my next multi family property as a primary residence close by move in, rent half live in the other and than rent where i am now which would cash flow upwards of 1k monthly, or i could buy another multi as strictly an investment property out of state which would be a lot cheaper (taxes and cost of property) and a lot more landlord friendly laws than New York, i guess i’m just undecided on which route i want to take and I’m trying to weigh the pros and cons of each scenario.

What exactly is their, "strict tenant screening & matching process"?

Also in case of fire or flood, I know a regular homeowner's insurance will have no problem covering it.I have been wondering, if the local regulation doesn't require it, why do we need pay thousands of extra for STRs?