I know for instance that something you just do to be polite like trying to help someone go up a stair can be regarded as discriminatory and you can be sued, so I am worried for those little things

I've used American Home Shield for several transactions and they have mainly been a neutral, but one instance led to them being MAJOR enemies, and one they stepped up and (though slow) replaced a $1,500 stove that was going to be at lease $500 to repair. 

Just wondering what others have done in this instance.

In certain instances, cash flow and appreciation share an inverse relationship.

Is college worth it, what exactly is the "it" in this instance? 

For instance, if I were to acquire a 4 unit in certain parts of SE DC it's considered heavily sought after property.

I can do a date down on the phone for instance that will be 95% accurate.. enough to make a go no go decision. 

Since everyone knows that, it is not a problem.Chicago is famously tenant friendly.

In instances of identity theft they can usually get their money back and if I believed it was real would work with them on a plan to get it repaid.  

NY is famous for Non-warrantable condo's meaning they are not approved by Fannie Mae/Freddie Mac guide lines and need to be underwritten and approved under most portfolio type loans.