Quote from @Andrew Cargal: I want to share my experience with The Mortgage Shop.

Many investors in NY like the idea of house hacking because:- They can invest with a low down payment (similar to what a 20% down payment would be OOS)- They gain hands-on acquisition, project management, and property management experience.

I feel that I don't have enough experience to know if I could do better or worse.

Now we're seeing investors pouring money into buying Class C rentals - but, many are getting burned.In our experience & opinion, the main determinant of property Class is not location or even property condition, those are #2 and #3.

It has been a very bad and costly experience. 

The debt is not yours, and unless a question is asked in a way that would subject every investor to having to reveal the debt of every entity he was an investor in, you should have no problem.This is based on my knowledge and experience, I am not an attorney.  

Airbnb 's app is clunky and more difficult to use than Vrbo's.From my own experience and what I hear from most others you are in the minority with this opinion.

Read a few books on real estate investing to learn the power of leverage.

Maybe the section 8 person can help advise you, but I'm certain they will give a disclaimer with anything they say that you still need to consult your own lawyer or read the rules.

The rest came with time and experience.