@John J.Well to address your mindset I think you are missing a huge factor in your fear of RISK as you have called it.The biggest question you you need to ask is, how many millions of dollars will I miss out on if I do not begin my investing career.  

Sit down and have an honest conversation about your fears.

That's what I'm grappling with -my own thoughts and fear. 

This happens every winter, along with the fear of the heating system breaking down and freezing our tenants or pipes. 

My underwriting has been too stringent due to my irrational fear of the next correction.

It's best to take a step back, look at what your finances DO afford, and how to make that a stepping stone, banks reward those who take smart steps and fear those who ignore caution and play roulette with their money.  

Do NOT make decisions based on this fear - it's literally verbatim what people (including myself) have thought and said in the previous two cycles. 

I really don’t know where to start but I don’t want my fears to hold me back from purchasing.

Fear of compliance is a myth and it's very simple when it's explained correctly.Adam Atassi 

You confirmed that some of my fears/suspicions may be valid.