There is no cut and dry answer to this, appraisers will ultimately look at condition and comparables 

@Lex Phumirat the answer to your question is not cut and dry.

Hardest mental hurdle for me right now is pulling the trigger and doing it.

BUT don't pull the trigger on something just because it's in your price range.

Some of the windows were just under 24” from the floor, which is what triggered the requirement.  

I've read the bulletins and guidance that with assignments, that is considered a transaction that triggers the transfer tax being due (again).

without triggering due on sale clause.

Two, in the north you don't have to deal with rain in the winter and snow is dry (As long as you don't get berried in it...)Three, rehabbing in the winter will make you ready for the spring when all the potential buyers are coming out of the woodwork looking to buy a house.

We hoped to save dry wall, but under the piles of stuff was mildew that softened the walls/ceilings.

Have you looked into short term rentals such as airbnb since you mention renting seems to be dry as well?