My biggest fear of investing out-of-state would be the fact that I will not be able to be hands on when issues arise.

My fear is worn out stuff like HVAC, roof, or plumbing eating future cash-flow.

One thing that's holding me back from purchasing my first property is the fear of "what if my numbers were not correct".

So assuming you're not crazy overleveraged and that you don't freak out if the value of a home declines when a recession hits, if you wait it out you'll be fine over the 5-7 year horizon. yes my fears buying cash and not being approved for refi and having my cash stuck in a property during down turn of economy.

Part of that is fear of overbuilding, which isn't the case for San Diego. 

@Terrell Garren This is my biggest fear, I can't imagine what could have happened if I was 23 living in this house.. haha!

My biggest challenge was my own personal fear of the unknown since it was all so new to me. 

After a year of fear and second guessing myself I sent a letter stating my search for a mentor to the founder of a local REI firm. 

Call reluctance is a common fear.

Better to be feared than liked.