Betting on appreciation is a real gamble.

Otherwise you are just gambling and will lose out eventually.Speaking from the perspective of a Property Manager... we do not usually manage home below the median rent rate for the city.

it's like gambling with people @Al Cordova some people are honest - and others are not.

I really need a 2nd job for now but probably a new job altogether in the near future, but I 1) don't want to have to quit my currently dwindling job just yet, 2) don't really want to work for somebody else, and 3) would prefer to work for myself controlling my own schedule, and everything else that comes with working for ones' self.The plan I'm considering is to purchase 2 or 3 quads using a HELOC on my own currently-paid off ~$150K home for the down payments, and me being my own PM (I have 30+ years of construction and repair experience, and some landlord experience).Would this plan count as 1) a job, 2) an investment, 3) a mix of the two, 4) a gamble, 5) I'm nuts, or 6) _____?

I don't have that kind of cash to gamble to that extreme.

How  do you manage to stay so POSITIVE when you're gambling?

It means that you are either getting emotionally attached to the idea of not letting a property get away, and/or your gambling demon has returned.

However, not everyone is comfortable gambling.  

If I'd put that initial investment nest egg against my personal mortgage instead of towards (what I later learned to be) a risky gamble, I'd have my home paid off right now, and either be working in town or putting stacks of cash away for when I will be working in town and can manage my projects.  3)  Find a good mentor. 

Buy and hold until you have money to gamble with- then try the flipping world when you have money to lose.