I have a good relationship with the property manager, and she has been responsive in the past.  

From what I've read and heard (and from common sense) it seems there is an inverse relationship between the quality of tenant and typical repair/turnover costs.

Build a relationship, so you can make sure they are someone who is going to actually take you down a road you want to go on.If I was financially ready to rehab/fix&flip houses, that's what I will be doing.Right now, I'm marketing for wholesaling.

My lawyer has a relationship with their lawyer so i would think that would benefit us knowing how things are moving along but it seems it's been the exact opposite.

As Jay notes, these can be 100% funding to established buyers, closing within a few days of the first phone call, non-punitive underwriting rules, zero junk fees (which borrowers absolutely hate), and the various accommodations that a personal relationship can offer if a deal takes longer to complete or has any issues.Don't minimize the relationship.

I would back up wegolook w/ establishing some relationships w/ handymen/contractors in the area of interest.  

You do NOT want to start out a landlord/tenant relationship on a lie.

While this property breaks the rules we've set for our analysis/purchase criteria, I wonder if it makes sense to build a relationship with an investor looking to offload a number of properties over the coming years (as we look to pick up more and more properties).  

Any recommendations on investor friendly agents perhaps connected with property management that have relationships with contractors or in house maintenance.

I think the good wholesalers know how to generate a large volume of leads and are able to pick and choose the best ones to present to their investor relationships.