Worst case, he loses the money that he paid for the option but walks away without exercising his option. (3) He should try to figure out why the seller is willing to do a rent to own or non-traditional financing.

Exercise careful due diligence and talk to references, and search the BP forums for key phrases such as "selecting a syndication sponsor" or "finding a syndicator", you'll find tons of threads on this topic with some great advice, like this recent one:  https://www.biggerpockets.com/forums/432/topics/503289-how-to-vet-syndicators?

The first one actually just reached out to me so I'll make sure to exercise more patience.

Needless to say, one medical catastrophe could wipe out all my hard-earned investments. 

You're practicing and exercising personal discipline in order to expand your business and practical knowledge.

You can be on the middle, be understanding with people in case by case scenario, if you have a long term tenant that is good and may have a sudden medical problem you can workout something with them about rent being late, but remember that if you don't charge for rent you are giving money away so see how important that is to you, can you afford to donate money to them?

Christain's response as fulfilling any of those adjectives you have exercised.  

(selling medical devices) so I'm trying to get into real estate ...

Might try in the medical district. 

I'll say this, if I didn't have rental income, along with medical benefits and compensation from the VA I wouldn't be able to do this full-time.