I am originally from UK and after 6 years I now qualify for funding and I am wanting to house hack a multi family (seems like a cheat code as it isn't an option on a residential mortgage in the UK) but the issue i am finding is the low inventory in my area (6 listings within 20 mile radius of Danville VA) and nothing that i think i can make cashflow well / or seems like it would rent to a decent caliber of tenant. 

If I were you, I would read the tenants rights document and then the actual code (New York Real Property Law Article 7 – Landlord and Tenant (public.law)). 

BUSINESS OCCUPATIONS AND PROFESSIONS Code Ann.

I recommend finding an accountant who specializes in real estate taxation and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.

More trouble than its worth unless you partner with an operator that specializes in it and can provide the expertise, nursing contacts, etc. 

we have 3 properties. but the best benefits to me are the message templates and automatic messaging and door coding, along with being able to handle direct bookings.

@Cliff SongYou can usually speak to a lawyer who specializes in LLCs without any cost initially. 

Which if youve done flips , but not commerical multi before, you wont miss much,  however a 6 fam is a commerical code permit so there are slight variations between the residential code for essentially all trades which if you dont have a detailed plan and you dont double check every code before you do anything but rely on cheap labor to do your due diliegence for you, what could go wrong ? 

-Get to know local code enforcement or inspectors.

My friend @Andrew Bosco specializes in medium term rentals (it should be similar furnishings to STR) and has a pretty sweet checklist that he utilizes for furnishing the property.