Completely get that it's a mostly personal decision, but it's comforting to know that one of them isn't glaringly terrible!

@Sam George, that's a terrible situation. 

The previous property manager was terrible and had barely any documentation.

I took out a small loan from family for a small venture only because my money was tied up but if it went south I had more then enough to cover it in by way of selling other investments so there was no cloud hanging over my head that if I failed, it would have been terrible.

I think both are terrible ideas, but I do think feeding a rental property is worse.If for some reason you get in a financial bind, you can always stop feeding the 401k and nobody cares. 

Warranty companiesThey offer a certain convenience but They can be a headacheThey can have terrible customer service/communicationThey can hire cheap helpAnd they will deny certain claims or just do temporary fixesSo why do people have them?

Yeah, hard not to get discouraged...after so many duds, its getting easier to think "eh, I guess a 5 cap isn't TERRIBLE" which I don't want to get into that frame of thought. 

We were buying property when we lived in Italy and it wasn't too terrible.

It’s just been a terrible experience.

This is what adds to the inconvenience of this thing - it's all outsourced to some LID collections group with a terrible web page.