@Scott Baker @Rhett Tullis @Eric Robinson
Hey Scott. I'm kind of in a position similar to you. I am new to RE investing, living in OKC, and soon to be moving out of state. I am looking at house hacking out of state vs buying a rental property here. I have a couple comments regarding your ideas and what others have said.
If going for option 1, be careful with the higher purchase price properties since you may be moving. It'll be tough to still rent out the rooms individually if your buddies move out, at which point you want to have the option of renting to a single family and still able to cash flow each month. Along the lines of @Matt Miller
I too have looked at doing the small multifamily route and house hacking with an FHA and have learned a couple things. FHA is very picky when it comes to 3 and 4 unit MFHs making you prove the income from other units will sustain the mortgage which gets difficult since you'll be living in one of the other units and the LTV will be really high. Plus until you refinance you'll be paying the PMI. The FHA route is more attainable with duplexes, a SFH renting out rooms, or with lower price tris/quads (which I'd assume wouldn't be the quality you'd want to live in.
Also, consider that if you are living in the property (whether it be 1-4 units), you could still get a convential loan and pay less than 20%. With fanny Mae/Freddy Mac you could do as low as 5% down for a SFR or 15% for a duplex if you qualify (strong enough borrower which sounds like you may be). You'd still have PMI but your tenants are paying it anyways. Then you could use the rest of your liquid assets to purchase an investment property (which will have to be 20-25% down depending on lender). Keep in mind that you'll need a certain amount of reserves (the banks I have spoken to said 6 months mortgage for the primary and secondary residencies).
You may want to consider shopping around some lenders and getting their take on your options. That and talk to some agents like Rhett to help look for properties that would fit your criteria and help you develop your plan.
With regard to your third option, I don't think that is a terrible idea if paying cheap rent. You could potentially find two great properties that with cash flow a combined $600 and now your rent is paid for. Consider what your goals are and what will best accomplish them.