If the boundary is not clear, if there is a fence in the wrong place, and other things that are physical then you need a survey.Waiting until later could be fine if you expect the damage later to be less than the damage now.

As a PM: to answer your first question, there is no reason your PM shouldn't be able to add the charge and credit it with out the money actually coming in physically to them, there for they should not have any issue paying the contractor directly and having it on your PNL. 

If you give them control, the tenants will take advantage of this.5) You have an advantage as long as they are not in physical possession of your house. 

If you try and interview without being in contract I know some will not talk to you because they physically do not have time to be talking to someone who has any interest in a property.

Would it behoove to physically see every home i wholesale?

 - "I own a physical asset."  

Even if their partner shares in the physical duties, such as drop-off/pick-up, doctors appointments, etc.

We both create massive value (him more dollar wise lol) but only I can physically feel that value.  

Our data sources may be incomplete or incorrect; also, we have not physically inspected a specific home.

If you have a guaranteed $10k/mo, I bet you could find a buyer for that income stream and if there is no physical asset, tenant or management risks, that is safer cash flow than a NNN investment.