They didn't pay for it, so they don't take care of it like an owner.Before you make assumptions about costs based on a seller's contribution to improvements, find out what they improved? 

Now, this would obviously be negatively cash flowing since you would need to pay taxes and insurance.

Keep in mind of the I/O(payments/period) and game plan on how fast you'd like to pay it down. 

Or, if you pay 20k over list price on a property that is 50k underpriced, you still got a hell of a deal.

With regards to your example about plaster vs. drywall most insurance policies no longer will pay for the plaster whether you have a public adjuster or not. 

Regarding your other questions:  - If the going value is $260/SF, why would you pay more than that?  

https://treas-secure.state.mi....some things to keep in mind:-Non owner occupied properties pay 18 mils more in taxes in Michigan - Even with the SEV you should plan that the SEV will go up.

I am the type of person that is normally looking to save a money to increase my investing so the thought of paying someone to do my taxes when we could do them ourselves didn't make sense. 

I’d recommend interviewing a handful of companies, asking for referrals, and making sure the team you choose has a multi-layer review process—so it's not just one person handling your books, but a team with oversight and checks & balances.And totally agree with @Markus Shobe: you get what you pay for!

Pay your attorney and your CPA for a customized advice.