@Sarah MooreI think there are 2 separate questions here - should you manage your own properties? 

This is a more affordable option but only protects against named events.Comprehensive Coverage: Often called “all-risk” coverage, this protects against most unexpected events, except exclusions like flooding or earthquakes, which usually require separate policies.

An LLC creates a legal separation between you and the property, so if something goes wrong—like a lawsuit or debts related to the property—your personal savings, home, and other assets are shielded.

This miscommunication almost always causes problems and escalating emotions. 

That said, it was easy for me to have my own custom site built through a 3rd party developer on UpWork, and then connect it to OwnerRez with their Wordpress plugins and short codes.I feel the cost is relatively small and worth it.I also pay separately for PriceLabs dynamic pricing engine, which I plug into OwnerRez, which for the extra $20/month, I find easily pays for itself.

They may write a separate umbrella policy.

And I love reading good advice, strategy and what have you...however we need a way to separate the bad and the spam from the good.

If you live in the illegal apartment, and it's separate, then what you've done is use an R-1 (single family home) zoning as an R-2 (duplex), and since that wouldn't be legal, the tenant may be able to successfully sue you for renting an illegal unit - even if you are in the illegal apartment - just because it's not legal to have 2 separate apartments on that property.I'm wondering if you could somehow rent it as a roommate situation, though, and get around that.  

Absence fraud, the success of the limitation will often depend on action which regard the entity as separate from the individual and other entities; separate bank accounts, attention to organizational structure, filing of entity documents, non commingling of funds, etc.  

If you have an Iphone, you can create a separate folder for your photos which you can save your business receipts.An alternative option is using an online storage platform such as google drive, dropbox, etcBest of luck