I live in San Diego and am trying to purchase my first investment property I have about 150K to put down but am struggling to find deals that meet my price point. 

Quote from @Derek Farmer: Hello all,I am 25 years old living in Indianapolis Indiana. 

If the property breaks even, or operates in the red currently, it will only operate deeper in the negative (unless you find a strong ROI like creating more bedrooms, convert a non living space to living space, etc) with another loan. 

How much depends on what you do for a living.

While you are willing to work with them, they are apparently happy to live rent free and don't seem to care about you.I had a long term tenant (5 years) who stopped paying the rent.

When you live in that duplex for 2 years and then sell you'll be able to take 50% of the profit tax free (the allocation for the side you lived in). 

I don't do this for a living and have no real world experience, but at 40% down, even with a 7% int rate, that seems like a high monthly payment.

If you qualify for both (you've lived in the property long enough and it is used for investment when you sell it) then you get to take both.

A little about me for context: I live in a very expensive market in Rye,NY. 

I live in Stamford, Ct and Fort Lauderdale, Fl.