As a property manager for over 5 years, I definitely know that it can be a tough and thankless job at times.There are specifics in your post that I won’t go too much into here, but I think a professional property manager would handle some of these situations differently.

I would think these are considered operational expense but with a 1031 I’m just not sure.

If I would not consider fighting this, it means few people would.I hope you knew this could happen as part of your due diligence when adding the JADU  Good luckThank you because it validates exactly what we were thinking. 

I think most places are in this range

This means if your friend offers $500k in “cash” for a property the appraisers think is worth $400k.

Just thinking out loud...

(I think the real ratio is about 50 bad ones to 1 good one!)    

If you are legitimately trying to start a real estate business, I couldn't think of worse advice to give you.

Quote from @Russell Brazil: So why do you think your tenant is telling the truth, .....

These were not our top 2 priorities but we're in the process of doing our due diligence and knowing all of the major and minor things people think we should look at will help us make sure we don't miss anything.