I've had several properties go vacant for a semester or a year early in my career. 

Hello BP friends, I want to set my career on a commercial/development real estate career trajectory.

It opened my mind to a new way of thinking and helped me take the first steps toward a new career as a real estate investor.

Your efforts now will snowball and catapult your real estate career by the time you're my age, so I commend you! 

Assessment of where you're buying and its 'frothiness factor'2 - Your need for cash flow vs longer term appreciation/equity building, mainly will depend on your time horizon with owning the asset3 - Your skills/ capabilities - some people are more naturally geared towards handling lower class areas, tenants, and usually the items that come up maintenance wise with this.The advice I usually give to 'youngins' (I'm 36 by the way) is to take the long view - which means the equity building, and your TIME to continue focusing on your career, building skills, etc - would lead me to be biased towards the property that you felt would hold / appreciate in value more over time.....

My job is secure and there is a good chance that I will be at this certain military base for quite some time due to my career path in the military.

I'd be willing to do legwork, tedious activities for the knowledge and experience- continue attending REI events, seminarsObstacles:- very little, to no savings- underwater in home; currently refinancing to MUCH better terms/ costsIn my favor:- decent size 401k- passion to succeed/ fight through hurdles- consistent regular career.

I am afraid to do a flip myself since I have no money- if I made a single mistake I could lose my college career.  

I just made a major career change; I’m entering real estate investing from a 9-5 in freight-forwarding job.

I have no exit strategy from my career - other than a 401(k).