A good lesson is to never sign off on a change order unless it has been discussed, shown to you, and you and he agree it is extra and the price is reasonable.

Personally, i would not be willing to got to that extreme for several reasons. 1- dealing with the city, inspections/permits, and contractors you're talking about serious renovation.2- is the RETURN worth the investment?

My goal with beginning real estate investing is to build some stuff extra income for now, and wealth for later.

You might find the extra coverage isn't much more. 

It's like "You chose to leave half of your furniture, but went the extra mile to unplug the fridge?".

I agree with Kim....make sure you get the right permits and that you also work with the county to rezone!

The problem was that the extra time started to weigh on me and I suffered from a bad case of "gottadoadealitis".

A win-win solution might be to charge some amount extra per month such that if they give the house back in the winter, you don't care because you have already made your money. 

'the popcorn ceilings are provided at no extra charge.

before careful of certain HMLs some of them have hidden fees and charge you extra during the closing statements.