I am debating between buying a single family property where I really want to live on long island (convenience, close to friends/family, location I like) vs buying a multifamily in an area in a NYC borough (Bronx) for the same price, but an area that I would not want to live (travel to work is worse etc).

Yup, live in Chicagoland and travel to Michigan to do all my investing.

I apologize for the tardiness of my reply, but I was traveling out of the country for a bit and had limited internet access.  

Hi All - new to the game here. currently rent and work in manhattan, plan was to buy a SFH in jersey and house hack to begin then possibly look to add duplexes to inventory. problem is I am not familiar with north jersey and my sights are sent on bergen county (ft lee/edgewater/cliffside park/palisades,etc) Can anyone help me understand the areas best to help me achieve goals, so far i've only travelled to teaneck and from what i've seen it is not a place i would like to walk out at night.

They're all located in the south suburbs of Chicago, so I won't need to travel very far to see each one.

I love my career and don't want to leave it, but I do want to get to a place where my fixed expenses are super, super low, so that if I want to strike out on my own and start a business, travel the world, etc.

The husband travelled for work a lot, so my showings had to be scheduled for when he was in town or when no one was going to be home at all.  

NOTE:  I may have to travel to enjoy this reward. :) 

Getting tenants to break their bad habits and accelerate their rent payments is always the end result.

We sent the bank an offer 80K below their ask, along with a detailed SoW of the work needed to make the building habitable (not to bring it up-to-date).