I'd rather be safe about it and ensure cash flow from day one.

Cash flow is important of course, but so is appreciation, so I want to ensure I have a balance of both.

Are there additional factors you think are worth considering?

I will also add that many independent travelers that do room rentals enjoy having their own fridge.To keep things kosher in shared spaces, my friend who runs PadSplit says every room comes with one colors or plates cups etc to ensure that guests are accountable for their own dishes.

Additional BZD $100 if they had to replace the concrete markers. 

Any advice or direction on how to go about this in Wisconsin would be greatly appreciated.Before you do that, ensure the home will make a good RAL property.

Quote from @Lionel Quiambao:  ... and maybe throw in the option for the tenant for more speed at an increased rent to cover the additional payment. 

I would look through emails or texts to see if you have any additional evidence to support your side.

It is currently a glorified finished attic with little room- Use addition and raise it up and extend it to the side of the home for more finished space and room for deck, washer/dryer room etc- Make the living space as functional as possible with the added sqft- Add outside living structures like deckThis is a fairly wealthily area and I want to maximize my ROIWhat are some things you recommend for a large scale project like this and what are some hurdles ?

I spent my entire summer doing maintenance and ensuring comfortability.