My insurance never even went up on two different automobile lawsuits. 

If you're a very prudent and fair person/owner, then most of your potential issues can be managed before they ever reach the point of a lawsuit. 

This Disney hotel incident sets the bar as to expectations and entitlements:8Disneyland Hotel Pays $100k Settlement Over Bed Bug Lawsuit | TMZ TV - YouTube

Would love to hear suggestions for providers that work well with STR managers, and if you think General Liability Insurance is enough to protect against lawsuits in the event a guest gets injured at a property I manage, or damage occurs to their personal property as a result of a leak, fire, etc..

If you fail to follow the rules, you may open your personal assets to a lawsuit.

Debra, keep in mind that if a major problem arises concerning your tenants and/or the property or a major lawsuit, the courts can take your personal bank account and hold you accountable, if you don't have an LLC or your insurance doesn't cover it. 

(But that could be a thread onto itself).Regarding the biggest issue here, using one bank account for only the holding LLC will save you a lot of extra admin work and bookkeeping, however, if I were a plaintiff attorney in a lawsuit where you are the defendant, the co-mingling of your funds amongst all your entities would be a easy way to show to the court that these entities aren't being treated separate and are ultimately an alter ego for you, in an individual capacity, and your structures (and underlying assets) could be folded into one big pot to pay out a claim. 

It has gotten harder because of unprofessional tax lien foreclosures leading to additional lawsuits by heirs who have not been properly notified.

Paying for a good lawyer is a solid investment because they'll help you stay out of trouble/avoid lawsuits. 

In short if you self manage and cashflow a bit great, but if you mess it up and end up in a lawsuit losing a bit each month and no having to deal with it will be better than a jacked up lawsuit because you didn't know what you don't know.Take it slow and be smart.