I just fear moving from here to there and having it end being low in supply.

You then need to get educated and informed by the right people which leads to the second obstacle- Fear : who to trust ? 

My systems of investing was called "Trial and Terror", my motivation was "Fear of Poverty".Now after 47 years of Trial and Terror, I still find myself learning about and perfecting unusual alternative financing and acquisition of properties and developing commercial real estate methods.We are developing two buildings on Charles Street now into, what might be, the largest Night Club in Baltimore.

Reacting to bad tenants, threats, or fear, will cause you more harm then if you sit back,  implement your lease agreement (according to the laws of your state), and let the courts do their job. 

Fear of market collapse 4.

The rehab is without fear because I will simply assume worst case scenarios, something that every average rehabber is scared of, "what is behind the walls" or "the unknown".

I find they could be covering up an unauthorized resident, property condition, or problem they fear they may be charged for......So it can compound a problem if you neglect these routine peeks in a unit.

If you have one, that should take care of your 100% vacancy fears.

Getting too wrapped around the axle about finding the ideal first deal is a good way to miss the game because you were too busy sitting on the sidelines wondering when to enter.sounds awesome. the second half of your post is nailing where i'm at right now: figuring out when to jump in based off of knowing that something decent is in front of me rather than waiting for great numbers in particular. my goal is to have something during first half of next year and not blow it, basically. if i break even, or anywhere near it pretty much, then i'll be happy cause of getting over the knowledge/fear/hesitancy humps.

Many in my generation are fearful of home buying until they are making big bucks because they lack knowledge and confidence with regard to basic home maintenance!