Unless, of course, you’re into character-building experiences.

Withoutknowing the details I can not suggest which would be right to add on.Several you should pay attention to are:- Ordinance & Law: Provides additional building coverage to deal with rebuilding costIncreases due to changes in Zoning or Building laws- Personal Injury Liability: Libel, defamation of character, wrongful imprisonment, etc.

I will not attack his overall character as I don’t know him.

It's usually best to talk with your neighbors about your plans and get their support as one of the variance tests is that the requested relief does not cause a public health issue or alter the essential character of the neighborhood.Try googling "tests for a variance in [your state]" and talk with your local zoning department.

Then, if you can trend over time you'll want to see where the "path of progress" is going/moving and attempt to buy in that path of progress to gain some appreciation in the future.

There simply are too many people attempted to get their hands in our pockets. 

I love the DIY approach—it adds so much character to a home.

Quote from @Landon Sheveland: Hello,My wife and I, are attempting to purchase our first property.

My managment company has made more than a reasonable amount of attempts to get the HOA to have this repaired. 

Or should we keep the one in Kaukauna and attempt to rent it out?