It's a long story; the job isn't ending cold turkey, just slowing way down such that I need supplemental income.

You buy a certain amount of coverage and that determines your premium, not the number of properties you have, etc.

Erie ins also has great coverage and rates.  

All the coverages/deductibles are the same.

I have seen several instances, however, where insurance isn't in place or a carrier tries to disclaim coverage leaving the owner exposed to liability.  

Hi Emily,I use Liberty Mutual for homeowners coverage and haven't had any issues.As far as type of insurance, you'll definitely want general liability and E/O.

Like anything in business, it can be complicated, but you CAN learn and understand it.Another (not exclusive, but potentially supplemental) way you can limit the risk is to get an umbrella insurance policy on your properties that will protect you by paying out for covered liabilities in the event your property incurs them.  

Currently I hold a full time job as an independent contractor working in supplemental insurance, and I have always wanted to create a stream of income from rentals and other creative investing on the side.

My agent just quoted me 1M coverage for $352 a year and he said this will cover both me and my wife. 

I will require the tenant to provide proof of sufficient liability coverage and whatever else their licensing division requires.