Your problem started when you gave in to all her complaints and unnecessary (maybe) repairs.

@Tom Gimer excuse my ignorance, but would you mind further explaining what you mean by "factor the cost of an unnecessary mistake into your analysis"? 

It's kind of like doing unnecessary repairs just to get the write off (doesn't make any sense.)

While these tours may seem unnecessary from an outsider’s perspective, the relationships with other agents and vendors is a significant value to the agent’s Buyer or Seller.

The list is endless in this respect.How about a life insurance policy owned by the company and pledged for a mortgage or as a buy out agreement with a partner, deducting that off your personal return in your name would be a trick.I think one company for every property is unnecessary overkill and (I forget the name of it) but Texas has an LLC that accomlishes this and I think a few other states may have adopted similar entities as well.

I would tend to think learning a new software just for business planning would be an extra unnecessary step.

$550K seems really high and unnecessary, but also don't want to make a poor decision in case something happens.I think I am going to ask for a version of the quote keeping the replacement value at $415K, but lowering the deductible to $1K instead of $5K.

Need to make sure I’m doing this correctly and not exposing either of us to unnecessary risk.

Because that is my own personal threshold for too much hassle for something that is unnecessary. 

You also have 2 sales, 2 closings, 2 transfer tax fees, and a whole lot of unnecessary risk if you got into a disagreement with your friend.