House Hack in NYC or Florida?

[Halil C.]

Hi everyone, my first post here.

I currently live in NYC (on a rent, one more year on the contract) and I am planning to get my first property this year. My ultimate goal is to make 5k/month as passive income (from rental properties) to retire early. However, I am going in between two options:

Option 1: Start with a house hack in NYC, live here one more year, and move to Florida to get my other house hack or rental properties.

Option 2: Don't house hack in NYC, move to Florida and house hack there and keep investing in rental properties in FL.

There are ups and downs to both options:

Ups of option 1: 

- I can check the properties in person since I already live here in NYC, I know the neighborhoods good enough

- Utilize FHA loan in a high cost market like NYC. If I don't use it in NYC for my first property, I don't think I can afford NYC in the future by using a conventional loan, due to high down payment. So this could be my only chance to get a property in NYC.

Downs of option 1:

- continue to pay high NY income taxes one more year while my job is remote and I could live in a low tax state.

- worried about bad renters so I don't want to lease the other unit in my house hack property to a long term tenant but also STR (Airbnb) may not be an option neither due to NYC restrictions on Airbnb

Ups of option 2: 

- Low income tax if I live in FL. Sooner the better for tax purposes, I believe.

- Might be able to get more than one property in FL without waiting 1 year since a) cost of properties are lower in FL b) can check the properties in person if I am already in FL

Downs of option 2:

- I don't know much about neighborhoods in FL (primarily looking at Ft Lauderdale area) so not sure about the actual value

- I currently don't live in Florida so not sure how I can remotely check the property given the distance. I have one more year on my NYC lease so I need to figure out subleasing or breaking the contract etc to move to FL and check the properties in person.

I am sure the list can be much longer but I just highlighted the most important info. 

My questions as follows: 1) Any critical info you can think of which I have missed above? In other words, what else would you consider while making a decision between options? 2) Based on the info above as well as your experience, what would you pick?

Appreciate any pointers, suggestions, guidance from the community. Thank you!