Mechanicals, roofs etc. can be towards the end of their useful life and pass inspection but then the cap ex can't be absorbed in many of these C/D neighborhoods.

Can you count purchases made by friends/family as expenses?

People will rent homes in that area because they cannot yet afford to buy, but hope to buy a newer home in the future and keep the kids in the same school system and around their same friends.

The insurer will probably also tell your friend (s)he appears to be in breach of the averments in the seller's affidavit and will be held responsible for any loss the insurer suffers as a result.  

Broker, friend connection.

Anyone have information about other similar brokerages that are investor friendly?

I'm also still friends with a great investor friendly agent in the area I'm sure he'd be happy to help.

You might need to build that skillset to show those family/friends you are able to do it.

Hey Ian, since you're not an active agent I would connect with some local investor-friendly agents in your market.

Quote from @Brandon Morgan: If you screw up a deal with a friend or relative, you will lose money and the relationship.