I know people sell occupied rentals but I don't really want to discount it and for the price that I'd list it I'm not sure it would be an attractive investment for someone else.

I see it once in a while that duplxes just split the actual bill, but those are usually owner occupied and nicer areas like Shorewood.If you rent units at or above median rent people have a higher tolerance for additional charges than tenants who rent based on a budget. 

Hey Todd,So the down payment for a Conventional Owner occupied 2 unit is 15% this will still have PMI as that is removed at 80% LTV.There are 2 options to get a down payment less than the 15%.

Are you still occupying the property yourself, or have you started renting it out?

(I assume a 203K is out because it's an investment, not owner-occupied, property, but I don't have a lot of experience with that program TBH.)If you're able to line up financing from family and friends at favorable rates, then that's more of a private money route which could make it more workable.

Originally, I was looking for a "house-hacking" situation with either a small home + attached living space (basement apartment, etc), or renting out rooms in a home I own and occupy. 

At the time you bought the property did you fully intend to use it as a STR and not occupy the property?

You'll notice that property taxes are automatically calculated based on millage rates for owner occupied vs. non-owner occupied rentals.Hope this helps!

FHA (FHA implies Owner occupied) will finance at up to 96.5% LTV, but there is an inverse relationship between LTV and cash flow (higher LTV = lower cash flow, lower LTV equals higher cash flow).With $150K and reserving $15K for closing and reserves would give $135K.

It can be more difficult finding a bank that'll do it for non owner occupied, but make enough calls (try credit unions in the area), and you'll get one.