This is one of those "no one is to blame" things that happen in life.My guess is that their insurance company is missing some facts.

Are we missing something obvious?

@Missy Luce I'm glad you revive this topic because I missed it!

His roof ‘inspection’ was done with binoculars and he missed almost a 5k repair that was fairly urgent—so you may not want to use that co. either.

I always discuss investments with others in an investor club because other people might think of things that I might miss.

AS a HML I have seen this play out with investors that drink the sub too coolaid and are simply not financially capable to handle issues when things go sideways.I have also personally bought over 100 sub to deals in my career..

If the answer is the latter, is it possible I would lose the money I think I would save by missing deals while trying to learn and upgrade my site myself? 

Not sure how complicated your situation is, it is easy to miss necessary elections in order to claim appropriate deductions.

Many will be missing out on opportunity to own a home.  

@Daniel Dixon If you're in Haughville it's kind of hit and miss.