Agents will use state approved forms that are standard for your state.Pros and cons to each relationship but I would presume the agent might suit you better.

What are some good property insurance online comparison tools?

I wouldn't mind the experience and training that is offered there but if the company's standards doesn't fit my aspirations I should try to attain a more fitting path towards moving forward, right?

I feel like I've heard that after a certain period of time you can convert it to a rental and buy a new FHA insured property. 3 yrs maybe??

So if income for a property is 2000/month, they count 1500 minus mortgage, tax and insurance.

What would your standard house insurance be for a 100k house in either markets?

These low down payments will still have mortgage insurance.

Payments currently are 2500 a month  for mortgage taxes and insurance and the place brings in 3000.  

Being a RE Broker you are held to a different set of standards and disclosure that if you were just a RE investor.

., but that's a question for the bank, not for the people here (unless they are the bank). each bank has their own standards.