Grad student turned REI seeking advice on first property

[Sheldon Vic]

Hello all,

Currently living in Hawaii finishing up my last year of grad school (I have a little less than 1 year left). Have a family of 4 and currently renting. My wife works full-time, while I have part-time work (not significant income; primarily financial aid), we will have no debt aside from student debt. My grandparents property just sold, which I will be splitting half of the proceeds between a relative and myself. 

I am working with a local REI/Realtor on finding our first property here. My goal for this is to eliminate rent, while preserving capital for our next property. I was looking into utilizing an FHA (down payment would be something feasible for a property <$400k-->refinance to utilize as cashflowing rental), USDA (no down payment, high mortgage-->refinance to utilize as cashflowing rental), or HELOC (interest only payment, then seek to refinance and utilize property as cashflowing rental) to acquire this property.

Once I graduate, our family plans on moving to Oregon, which we would seek to find our next property (live and flip). I am also interested to invest out-of-state with any extra equity.

Ideally I would like to keep the Hawaii property for appreciation with potential cashflow (worst case im temporarily breaking even on the property, but having mortgage paid down and gaining appreciation).

Does this sound like something that could work? Thanks again BP community!