First I would say that it's OK for this to cause you a little anxiety. 

First off, nothing of significance comes "easy", everything can be learned and look at it as a game to take away the anxiety and fear that comes along with it.

Thinking for a new home is a source of anxiety, frustration -- and a huge sense of accomplishment.

Also search for Distressed Mortgage expo and NoteworthyBooks: Invest in Debt - By James Napier (oldie but goodie) Performance Anxiety by Gordon Moss

I can see how raising rents and possibly losing a good tenant can bring anxiety but at the end of the day you are losing money by not asking for market rents.

Some other good reads are:Performance Anxiety by Gordon MossTurning Distress Into Success by Fuquan BilalInvest in Debt by Jimmy NapierThe Art of Investing in Distressed Mortgages by Sherman Arnowitz The Banker’s Code by George AntoneThe Wealthy Code by George AntoneFour Step Guide to Private Lending Profits by Lee Carney Harder Working Money by Jay Leigeber

I genuinely enjoy all those things.She is spared the anxiety of my decisions until it's too late to worry about it, and that's how she likes it.

Having anxiety about screening a good tenant is normal, wanting to know invasive details about their life to feel comfortable isn't ok.

Sure that may be "risky" but tenants want certainty and leaving them in the dark contributes to anxiety.

He has major anxiety problems and this is too taxing on him.