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).

I know this is far from ideal.

Upon completion of rehab, or once tenanted with a lease is ideal. 

Ideally you should underwrite several scenarios and see what would work best in your case.

Ideally would not live there more than 3 years. 

(and the sub section on REAL ESTATE MARKETING TOOLS & TECHNOLOGY TAXES & ACCOUNTING LEGAL TEAM)Bonus for the weekend, my collection for starters (read the comments too, and then if you like the author, go check out what else they wrote):https://www.biggerpockets.com/renewsblog/stages-of-investing/-https://www.biggerpockets.com/renewsblog/newbies-learn-real-estate-investing/-https://www.biggerpockets.com/renewsblog/5-ways-to-know-youre-not-ready-to-invest/-https://www.biggerpockets.com/renewsblog/ideal-vs-desperate-investor/-https://www.biggerpockets.com/renewsblog/how-much-to-offer-property/-https://www.biggerpockets.com/renewsblog/hazardous-attitudes-of-investors/-https://www.biggerpockets.com/renewsblog/2016/05/31/21-traits-scammy-real-estate-investment-guru/-https://www.biggerpockets.com/renewsblog/youre-not-cut-out-to-be-real-estate-investor/-https://www.biggerpockets.com/renewsblog/questions-new-investors-should-ask/If this not enough to get you started and keep you busy ...let me know and I'll send you a list of blogs, podcasts, and books. 

@Jorge Leon Jr, I understand the ease and sense of security that comes with not having a mortgage, but from a purely financial POV, it isn't ideal.

Two of the tenants seem to be ideal with rent being paid on-time, considering it being put in the mail, etc. 

@Michael Newman ideally your W-2 job would serve dual purposes, both focused on your passion... 1) build capital and establish credit worthiness with which to pursue your passion, and 2) give you experience in a career you're passionate about. 

ideally a 1st position lien.- Tom