Now that I've been enlightened with BP, I've now been more open to the idea of "managed" risks. 

Essentially, we would lose money on the house, then risk all the greatness that comes with renting on what we would like to be our home for a considerable amount of time.

Tried to mitigate risk by using the AHS which did come in handy for potentially expensive AC repairs which I didn't need to pay for. 

Get a permit, liability and risk isn’t worth without a permit, who will inspect it if not the city?

Chip Cummings' book on Zero Risk Real Estate is a possible place to start.

A lot of investors like Multi  unit properties for economies of scale, and diversified risk. 

In fact, for one of my rentals, I found it cheaper to pay for the preventive removal of a sketchy tree on my neighbor’s property rather than wait for the tree to fall on my house (and risk the tenants getting injured).  

This happens all the time, risk we all take. 

I don't really have time to get multiple quotes since this needs to be fixed ASAP (tenant currently cannot shower as it is backed up).He claims that putting "copper sulfite at the joints" will "eliminate any risk of roots growing around the new piping." 

Please don't take that wrong, just trying to help you save time and eliminate risk of misunderstanding.While services differ somewhat, all self-directed plans are governed by the same rules outlined in the tax code.