This just seems like it puts me in a potential bad situation if something goes wrong during the process.  

What could possibly go wrong lol!

I don't think there is a right or wrong here.  

Telling sellers everything wrong with their house and justifying your offer with repair costs doesn’t build trust—it kills it.

We don’t know any PMCs to recommend in the area mentioned, but since selecting the wrong PMC is usually more harmful than selecting a bad tenant, you might want to read our series about “How to Screen a PMC Better than a Tenant”:https://www.biggerpockets.com/member-blogs/3094/91877-how-to-screen-a-pmc-better-than-a-tenant-part-1-services-and-processesWe recommend you get management contracts from several PMCs and compare the services they cover and, more importantly, what they each DO NOT cover.

Account Closed a PMC has two options to get liability insurance (tenant slip & fall) protection:1) Get added to owner's policy as Additionally Insured (NOT named insured).2) Setup a master commercial policy and add every property they manage to it and then charge those owners the cost of the policy.Otherwise, a PMC CANNOT get liability coverage on a property they have no ownership interest in.So, nothing wrong with their request.

I could be wrong or out of line, but I feel like this is a field where you really need some good expertise/experience to know how to address the variety of crazy situations that will come up.

Hi, Anthony, yes, I have had a lot of trouble with DM returning incorrect data - wrong owner or owner not found, wrong or no mailing address, very few sale dates, and now when I filter on lead status, it does not return all leads with that status.

The vast majority of lawsuits against Landlords are for wrongful eviction, security deposit disputes, and Fair Housing Violations.

Your best bet is to find and contact all of the top local wholesalers and go to work for one of them and see what they do right and wrong and see if it's even a business you like.