I had one rental in Baltimore which is built in 1956 and is insured with Allstate. 

1.Ask for a copy of their standard seller side and buyer side closing documents2.Ask if they close any non-traditional type transactions you intend to use.3.Ask for a copy of their standard fees, and if title policy rates are not set by a governing body4.Ask about insurance premium rates.5.I would ask them if they are investor friendly.6.If they double close and if what do they, ask what do they charge for the 2nd close?

I am updating a rental agreement.  The current agreement talks about mailing checks to our address, due by last day of previous month, etc.  We are now moving to automatic draft from their account.  I'm interested in ...

Based on some properties I've looked at the mortgage/insurance payment would be about $500-$600 so combined with my rent I'd be paying around $1100/month.

You will pay mortgage insurance either way for the privilege of putting so little down on properties. 

The agent has to go into the hudhomestore website and fiddle with something and that triggered the auto-email. 

I would ask your insurance company, I know my insurance company had some issues when I had 4 names on a lease that didn't share a last name for a SFH. 

Personally I'm keeping the one rental I have now in my name and using a well known insurance company with a solid insurance policy to cover me.

Im in a similar situation with a municipality, but if you are able to cover health insurance through the service, that makes the transition out of the traditional W-2 much more feasible and also covers all of your bases.  

He also said that I will get dropped as a client if I hold the insurance company to their $1k deductible they quoted me.