We have a PM, but I also have built relationships with other professionals (landscaper, flooring guy, HVAC guy, painter, handman, etc.) in the area because I'm more comfortable with the vendors and contractors that I have had complete work on the house before.If doing everything yourself, I'd imagine that "how far is too far" is really only a function of your own tolerances. 

Without knowing all the details of your situation, I would say you are on the right track looking into the real estate professional classification for your wife.  

I agree, those porches are frightening in their current state, but even fixed up how much functionality would they have?

Obviously big fancy nice houses, but what's the lower end of that classification?

She has zero interest in Real Estate.. compare that to some mid west factory... your not going to find fully functioning restaurant in the facility feeding people for FREE .. free day care FRee massages etc etc.

If not,  adding it to the second floor,  as long as you have a functional space for it would be the best option. 

Typically, they are classifed as Defendents as well when named in the foreclosure suit.  

there is a Risk=Reward function  I get that you need a higher Paper return to justify those properties.

It's also a collective decision on the functionality of the home.

Fundamentally, it's not a bad deal financially, depending on the deferred maintenance needs (if any) and the functional life of the major components.