Point there is, whatever you think will happen, expect that there will be an obstacle you must overcome in every situation.I am 38.

Get used to hearing no over and over again; overcoming failure is the difference between successful and unsuccessful investors.

There is always risk, so learn to manage risk instead of avoiding it"As a risk adverse person, I am trying my best to practice this second quote.  

Probably, but it likely would have taken me several more years and I don’t know if it would’ve helped me overcome certain fears about investing in real estate for my wife. 

If you are risk adverse real estate, (especially out of state) is not for you.

What were your pain points and how did you overcome them?

It's less about beginner/advanced friendly markets and more about what downsides you're willing to or able to overcome. 

If your credit is not too low(i.e. below say 550), or your don't have previous adverse credit actions(foreclosure, etc). 

I read a lot on real estate too, but wanted to branch out for some variety and particular focus on biographies to get better ideas of the challenges that they had to overcome. 

For the home buying portion of my market, a large portion of the buyers are retirees from larger metropolitan areas that may be retiring with pensions or large retirement funds, thus not as adversely affected by current financial market conditions.