The caretaker would be required to assume paying taxes and insurance plus upkeep.Both units need a fair amount of work prior to being rentable now that it’s been vacant so long.

I am trying to get the best affordable quote for Landlord insurance.

That's one of the reasons tenants should have renters insurance because it covers things that may go wrong but where the landlord isn't responsible to compensate them. 

Realtors have companies and insurance to cover lawsuits.

I would greatly appreciate your input on this matter.Here is my setupPurchased property under a TrustLLC in FL owns the TrustHolding company LLC in WY owns LLC in FLI purchased the property sub-to, took over the seller's mortgage and I’m working on setting up insurance for the property.I understand I need to keep the seller as additionally insured in my insurance, but the seller no longer has "interest" (ownership) either in the Trust, nor any of the LLCs nor in the Deed nor Settlement Statement.

I ran the numbers and it looks like our house would not cash flow (between $0 to -$300 /mo) as a rental, mostly due to the astronomical property tax and insurance rates.

I have had a lot worse and never been forced to replace it to get insurance.  

Most of the time, you're not doing anyone any favors by keeping rents too low - you're running a business and taxes / insurance / HOA / Maintenance are likely to continue to increase.

Hi BiggerPockets Family,I am looking to insure a triplex that I own in Philadelphia which is under my LLC. 

Why wouldn’t you get an umbrella insurance policy instead?