There is always risk but I strongly believe if you have done your homework, your property is up to code and you are a diligent landlord you have very little chance of having problems. 

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.

In the Colorado market, knowing how to structure and sell an offer for maximum impact is really the difference between success and failure.This is something you will never have with a green agent who has the time and willingness to write 100's of 1% offers...hence, both your time and theirs is completely wasted.I know this doesn't answer your question about how to convince an agent to do all that work for you with little chance of return on their time, but hopefully it gives a little more context to all the answers above that say in one way or another, it's probably not the best route for you to take anyway.

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

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?