It is hard to ask other people what is and is not a good deal when you are not clear what your end goal is.I fell victim to this and now when I help fellow investors I really stress that having the right mindset is the most important thing.

Sometimes they will be experiencing legitimate money stress, in which case you can advance them a portion of the payment, but don’t give them the full payment.

Needs everything, foundation bad, so floors are bowed & stressed, all flooring is worn and damaged, as is drywall, windows, entire bathroom, entire kitchen, doors, plumbing, electrical, roof, siding.

But I decided that it would help me feel less stressed out personally...and it will be freeing up an additional $1500 per month - which if you figure - COC ROI = 20%.  

I think you're stressing your brother out over what probably is nothing Joshua D. . 

You have to be wired a certain way to be a (mostly) stress free landlord, but even more so when working in more sketchy neighborhoods.I hope to one day graduate to more properties in better C and B neighborhoods (and look forward to more appreciation) but next year I hope to buy another three or four of these low income properties.  

Some people hate debt and if it's going to really stress you out pay cash for it. 

Didn't have a financial set back but had lots of emotional stress all learning.  

Maintain at least 6-month of cash reserves to cover expenses and review your insurance liability coverage to confirm you are adequately covered from a liability risk event.Just like the Federal Bank stress tests that gauged how well prepared the large US banks were to another recession/depression.  

While its a statistical fact that many more people died around or just after the holiday season (stress from family dynamics, lifestyle, drinking and eating habits) this does not correlate to a "probate season".