While you are occupying the property your mortgage is being supplemented by the income income from the other units even though you are not cash flowing you are making money as a form of savings .

@Jared TownsendThanks - with the $100K liability coverage limit, why not supplement that with an umbrella policy?

I want to own property that brings in some cash flow that will supplement my current W2 job with the goal of retiring early.  

If you can't supplement on nursing sites (like furnishedfinder.com) then yes you might have to convert to long term rental come Sept but this would give you the summer to try and make the difference if things open up. 

Rentals to supplement your retirement income are an obvious option.

Depending on the turnaround you. an supplement you rehab cost with credit cards.

I have a kind've wacky idea about using RV's to supplement cash flow. 

You are in a 1BR apartment comfortably for 1.4K so see if there is a property with say a 2-3 car garage that has a mortgage of about 2-3k a month and you could rent out the garage space to supplement income.

Supplementing tenants rent is a welfare mentality not business.  

Renting to faculty, out of state students, students from abroad and more of year round (such as residency) students will not carry the same short term renter displacement, but may require a higher level of finish in some cases as this becomes a year round home.Perks here are- -Year round rent under the same renter/ as your lease terms apply-Some renters having supplemented housing stipends paid in the form of allowances, stipends, and other arrangements -Lesser degree of potential property damage for those in graduate/residency programs (simply based on age and maturity - again, use the automobile industry here in why most car rental places won’t rent below age 26)-Less need for obtaining co-signers (allowing tenant to solely establish some credit history as well)When your tenets do move on and out, as a ‘thank you’ for being such great renters for the span of their academic career, it can be nice to offer a letter of reference as well for future renting needs.