But these expenses are 100% necessary compared to a lawsuit that would subject my other 10 properties from any negligence from the 1 that may have an issue.  

Anything that constitutes a major inconvenience to the tenant, such that a reasonable court would find one negligent for not addressing quickly, constitutes an urgent maintenance need.Example of the former: leaking water, gas, exposed live electrical wires, smoking in electrical panel, dangerous leaning tree, etc.Example of the latter: poor heat performance of heating system; clogged gutters overflowing causing basement dampness; etc. 

Some states allow for a tenant to "evict" themselves due to landlord negligence. 

If you are personally handling the property and do something found to be negligent an LLC will not prevent you from loosing a lawsuit.

Imo - not a lawyer so take it for what it is and get legal advice if unsure.The llc will help reduce risk however if you are negligent you can still be held liable.Talk to other people, get llc for dummies.Here in ny pretty easy to setup.  

Nothing will protect your assets in the case of a negligence lawsuit which most lawsuits are about.

I suppose I can talk to my insurance agent, but I'm not sure if allowing smoking with oxygen nearby would be considered negligence or otherwise invalidate coverage in the event of a fire.

A lot of people aren't aware that a a landlord can file a claim against the tenants insurance company in cases of negligence.

Whether or not this is because of the negligence of the portal or because that's the nature of investing is something that I am sure will get argued forever.  

If it's caused by their negligence, then they will be billed for it.