@Dominic Pizzi when I was starting out, I bought a B-grade property every year that I house hacked (I had housemates). ...if you can tolerate having housemates (or living in a duplex/tri/quad with tenants next door), then this is often a better approach than buying a property with an investment loan, because you get all the advantages of an owner-occupant mortgage (lower DP, lower rate, better terms all around).Also, you mentioned student loans.

Do I consider them occupants, even though they only live there every other weekend?

If I conservatively estimate 50% occupancy, the total income on the property will be somewhere between $7,500-$9,000/mo.

We're at a 93% - 100% occupancy rate per month.

Especially if you go out of state, you are losing big bucks to the PM's who rrip you off and laugh on the way to the bank plus your rentals will accumulate a very bad smell due to the nonperformance of your PM's who totally ignore the occupants and dont even know they're stuffing the property with squatters.

The city gladly collected the occupancy tax from these STRs. 

Increase your neighborhood value, better tenants, etc.And please make sure the property you acquire has a correct certificate of occupancy with the city.  

With enough of a down payment (and assuming the property is not owner occupant protected by homestead laws), and with good buyer credit - that there is limited risk for the seller.  

So they sell to an owner occupant (because as we just said, the landlord is selling because rental rate is incompatible with renting it out.) so now there’s one less rental.

One is at 65% occupancy and the other was at 20% occupancy.