You hit a couple home runs, a triple, some doubles, singles, and maybe took 1-2 losses. 

@Kevin SiI would use the $1 million as a down payment to finance much larger projects like apartment, buildings or triple net lease commercial property.

Rent paid for all of the expenses, so it cost me nothing and over the years (I kept it for ~20 years) price almost tripled by the time I sold it.Not sure what grad program is 3 years (I'm used to 2 for masters, 4 for PhD), but if you do need to sell one, I'd look at each property and see which one has the most equity, highest interest rates, lowest return, major expenses in the near future (eg new roof) and you mentioned you'd lived in two for 2 of the last 5 years, so have capital gains exemptions. 

Most of the condos have tripled now.

WH, Lee Harvard, all areas that have tripled or more in pricing.

Most owners of short-term rentals on the islands and the nearby areas have been dealing with the triple whammy of a slowing economy effecting rental revenue this year, higher insurances and higher property taxes.

Triple Net Leases have caught my eye as a good possible investment.

Again some people will tell you that is stupid.Then by some ‘expert’ I’m a triple moron.

Property taxes will INCREASE after you buy a property and often double or triple from what they are now.

HMM " BEST BET" hmm, everything in clev over the last 10 years has tripled quadupleld or much much more, on top of the 30% net caps.