Because the cash flow isn't that great due to HOA, I am hoping to find a PM who is competitively priced with their fees without sacrificing quality.

If you're evaluating property to invest in, I would recommend finding a quality broker to assist you in evaluating that property, and others, to make sure you have as much assistance as possible related to a large investment.

We would plan to keep our current home and rent it out as well if we did this.I appreciate your insight on the tenant-landlord relationship, makes sense to target a better quality neighborhood to hopefully prevent some of those issues.

Find a local investor friendly Realtor, ask them for a referral to a quality local property manager and have them help you find a duplex that needs some cosmetic updates.

Those are all computer algorithms that can't take specific details into consideration like paint color, flooring, countertops, room layout, quality of neighbors, and many other factors.Use their numbers as a beginning analysis but then actually look at comparable rentals on the market and compare them to yours.

To add to that, where high income people are moving. 

I highly recommend you get involved with local real estate meetups where you can learn, Network, and sometimes find a deal. 

DOB (on photo ID)**I would highly recommend using a tenant screening service so that you have a full application and ability to provide details to a collection agency.

I'm worried about how much penalty I'll have for using my insurance.Or, do I save on monthly premium and hold a high deductible, and pay for a new roof out of pocket once it fails? 

AirDNA just released an article on this that I'd highly reccomend reading.