We were renting to my step-daughter (no lease) at a discount and I told her she probably needed to move because I needed to rent the house out for $1,600 a month (market rate for this house).

Thanks,CédricHere are the details for both policyA) Statefarm policy: Quote effective date: 04/11/2018Term: 12 Months COVERAGE DESCRIPTION LIMIT/DEDUCTIBLE PREMIUM A - Dwelling - Fire: $ 171,900 $ 222.00A - Dwelling - EC: $ 771.00A - Dwelling - VMM: $ 24.00 Other structures: $ 17,190B - Personal property - Fire: $ 0.00 Deductible: 2% Deductible Fair Rental Value (TDP-017): $ 1,200 $ 65.00 Cap on losses from certain acts of terrorism (TDP-820): Yes DISCOUNTS/SURCHARGES LIMIT/PERCENT PREMIUM Claim history discount / surcharge: $-216.00Volunteer firefighter assessment: $ 0.00 TOTAL TERM PREMIUM $ 866.00(Note I can get 1% deductible for $1,064)B) Lonestar policy [though United P & C (UPC)]

Taking all that great info, then going to a discount brokerage, isn't exactly behavior that encourages agents to be helpful, big picture. 

Though your HOA fee seems reasonable, you still give up control and it can go up or you could get hit with special assessments if it is underfunded.So, if cash flow is not great, and appreciation isn't likely to be great, the only thing that leaves you as a return is mortgage paydown, which is not to be ignored, but will take a LONG time to add up and I think you could do better.So, I'd consider downsizing to a smaller, less expensive house (which sounds like your plan anyhow), where the numbers as a rental would look better, without a HOA, that is cosmetically challenged and maybe a REO so you can buy at a discount and put in some sweat equity, smallest most rundown house in a solid neighborhood, and eventually (maybe if/when the market dips next) turn it into a rental and buy your next place but fix it up and save like crazy in the meantime.

We had a tub done and it was about $450, but we negotiated for a discount and got $100 off.

I may make an offer contingent on the owner discounting rent for the three vacancies and getting those filled.

It certainly makes it a lot tougher and I'm not discounting that, and I'm not saying you should house hack.  

In this case I don't think you can discount the institutional investors.

I have a discounted building supply store In my area.

I don't think you will get anywhere with saying to a seller "well because you lied to the IRS, I think I should get a discount on the property."