Long story short, I found a couple who had a wholesale deal that they were looking to offload.

Be careful with the short closing times, sometimes escrow can't get Title or the payoffs (if there's a loan on the property) quick enough. 

The longer the gap in insurance coverage, the higher the future insurance premium.

I'm about to close on my second property and ideally would like to find short term tenants to get me on my typical June-May rent cycle (I rent to students).

For me the key is evaluating and locking up a contract in short order is the key to getting good deals. 

My short term return estimate relies heavy on return by the value add.  

I read a SF short story not long ago about a senior companion robot, how easy is that to visualize!

Intent is to live in the largest area of the house, rent an already existing basement apartment on short term rental, add a bathroom and kitchenette to two finished rooms in the garage and create a second short term rental, and then put a yurt in the back yard with sole access to another bathroom that'd be installed in the garage as another STR. 

Long story short.

So, Decide which kind of investor you want to be (SFR, Commercial, Land, Tax Liens, Passive, HML, Multi-Family, Notes, Fix & Flip, Buy & Hold, "Subject To", apartments, duplexes, assisted living, REOs, Foreclosures, Short Sales), etc.