I am guessing yes cause you want to use it occasionally, so much more energy spent in managing lots of turnover.Whats the insurance like?

Talk to your insurance provider before deciding whether you want to adopt a policy of accepting dogs.  

The mortgage has a small balance of $22,000 with a $232 of monthly payments which includes principal, property tax, and fire/water insurance.

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.