Basically he is proposing the same thing he did prior  -  when he put $1600 on a $34,000 note and then made no further payments, all the while he lives in the property as it continues to deteriorate?

Being around her leads to anxiety attacks and just overall deterioration of health; it's like living with a soul snatcher (lol).

The inspection revealed a pinhole leak, deterioration in water main.

Assessing and correcting water management around the exterior of the foundation may stall the deterioration sufficiently that you can operate for a few years before a "big dig".Does the 20K electrical estimate include relocating the ill placed panels and rewiring everything?

In the case of a manufactured home, it is closer to personal property and will only drop in value as it deteriorates.

Our investment scheme is that we'll buy a house with nearly any problem, just not every problem. ie, if the roof is bad AND the foundation has issues AND the siding is deteriorated AND it needs windows, then we probably don't buy that.

I've dealt with asbestos siding before, inspectors in the markets I operate in tend to not be too concerned with it if the integrity of the siding isn't deteriorating heavily. 30k to replace it sounds insane, though. 

Also, I would guess if you took a national poll on whether "Chicago" had deteriorated or improved in the past 5 years, more would say deteriorated.

If it was already old or deteriorated at all, then you may not owe for a whole new one. 

I pulled the subfloor up to sister up the joist and get the floor plumb but my contractor just reported that all the wood is deteriorating and falling apart.