The property will have two key Target Markets: A house hacker as bottom unit could be a great rental, Air BnB.

I agree with @Gene Hacker about the valuation of multi-family properties in the state. 

@Daniel Haberkost No my coworkers aren’t house hackers.

This doesn't mean you cannot succeed as a newbie, it just means you have to bring tremendous value to prospective home sellers in order to get deals done.Many newbies in Brooklyn, Queens and other parts of NYC begin as house-hackers.

It was pretty smooth since I bought directly from the seller.However, I work with a ton of house-hackers now as a Realtor in New York and I see that most of the barriers come from either financing or title. 

You could however and then the rules explained above will apply: most lenders will give you 75% of the appraisal (a little lower than 80%, because its a duplex).A lot of my younger clients are serial house hackers and I have heard the line "This is the last one, the next house will be a single family) more than a few times, and usually it's another duplex (typically in a nicer neighborhood like North Shore or Tosa).Another note: Milwaukee's inventory does not lend itself very well to 4 family house hacks.

Your VA benefits give you a leg up compared to most other house-hackers, so YES, make sure to use it to the fullest! 

I'm looking for my first house hack I'm located in the Tampa area. I'm thinking about investing in a rehab and turning it into a house hack or a live in flip, guess my question would be, where in my area should I narr...

You're an elite house-hacker. 

I thought I was some kind of uber hacker when i figured that out (purely by my own incompetence originally though) but it probably no longer works.. maybe it really was a legit multiple bid situation, but it always seemed to work for me.