I feel that this will hinder her chances of being a long term tenant.

There is a pretty good chance you will have to deal with this same issue over and over again unless you can make a good friend with someone on the HOA board.

They also see it as a slim chance to get the deal done so they lack the confidence to really work with you.

Also, based on his experience he probably knows that the chances of having 5 offers accepted can be low depending on how much you're offering versus how much the Seller is asking.

I have a family realtor that I use to look at turnkey properties that I'll pay market value for more times than not, but I don't want to burden their time making 100s of offers a year for me if only a percentage of those will ever bare any fruit.  

(Life hack tip - "Change is inevitable, change is good, embrace chance!")  

We plan to split the extra rent above the base rent of $1800.Preliminary results are that it is just barely worth the extra work.  

There is an unbelievable wealth of info on Bigger Pockets if you haven't had a chance to explore it.  

I was in a rural area and had little chance of getting help there.

Or by chance sooner because there are multiple properties?