I also know that the lower prices to be found in NY have a lot to do with there being older buildings, higher property taxes, tougher neighborhoods, less appreciation, etc. which I know I will need to incorporate into deal analysis accordingly and understand the risk of.Summary: I feel that with having to put 20% down (FHA loan house-hacking is pretty much out of the question in NYC due to the astronomical prices here), buying a property in New York may be more attainable with my current savings and would allow me easier access to visit the property, however I don't think I could afford the quality of property I would like (close-ish to turnkey) in Florida.

If your price point is about 2k you are probably best served putting it on the MLS as most of the people that can afford that rent are often going to become buyers and will be working with an agent already. 

Although many lenders do not offer this type of loan, those that do are a great option for real estate investors who are unable to provide the stricter guidelines of a traditional loan.The relationship between the borrower and the lender is based on the idea that the borrower will be able to afford and be able to pay the loan payments.

There are also areas around issue that are more affordable and experiencing a lot of growth that could potentially work for you. 

They are fairly affordable and provide superior connectivity.

When you look at the data from last year, you see millennials looking for deals and voting with their feet moving to places with affordable housing like Detroit and Austin.

However, I also see a multi-family property as an ideal candidate for higher income in the short term to allow me to be able to afford purchasing additional homes within a year or two.

Will allow for renovations while living in the property and can easily afford $1,350 a month.Thanks in advance for the help!

The land business is doing great, it's more beneficial for my long term wealth strategy to take the tax savings and I can afford to pay private money (friends/family) to fund the land deals. 

If you are going to invest in more affordable areas, definitely pick up David Greene's book Long Distance Real Estate Investing: https://store.biggerpockets.co...