If they don't set it up correctly, they could lose a lot of anticipated income and have to foreclose.Disadvantages to the buyer include, if it isn't set up correctly and the seller dies, ownership may be in question with a long painful lawsuit.

I got family that couldn't evict a tenant for almost a year that was extremely painful, and I wouldn't want to go through that.  

I spent almost a year getting my hands on a 4plex, there were several times that I thought it would be a pain and I should buy something else, but everything else I looked at made this a good deal.

Having more homes does help spread out your risk, makes repairs and turn over less painful.  

It pained me that I was not able to be at my kids’ bed side daily, due to working multiple jobs to provide for the family.

Navigating the forums is a bit of a pain in the ***.

Trying to sell a house with electric heat in the midwest is going to be a pain point for many buyers. 

Do you have any pain points you wish software solved for you?

I got $50k off of one deal and $35k off of another recently and it is a painful process for the seller (Both properties were under contract for $150k or less). 

As you have already found out, non-warrantable condos are a pain to get financed.