Financing question (rental or house hack first?)

[Burke Fisher]

Hey guys I have a question, my fiance and I have been into real estate investing for the past year. We have a flip project going on in Atlanta and now we've been thinking thinking about house hacking something around ($250k) and finally getting out of our apartment, we already have a close friend who would rent out the room/apt/duplex but we also really want to get into one of our local rental markets and purchase a cash flowing SFH since they are so cheap and its on an army base (PP:$100K Rent:$1,200) (we would do both of these conventional) so my question is, should I purchase the cheaper rental first and get it cash flowing then go onto either buying a home or buying a home to house hack? Just don't know which one would look better to a loan officer. Please reply with your opinions or experience! Thanks Guys!