I started working in the trade doing construction and plumbing on my summer and winter breaks from college. 

It is going to need new plumbing, electrical, sheetrock, tub, vanities, hvacs, flooring, framed doors, door handles, cabinets, sinks, trim, and the exterior will need at least scrapping and painting, probably lots of rotten wood.Just the plumbing and electrical is going to be about 25k.There is a reason that the property is still on the market after almost 2 months.

I came across your post and with my knowledge of plumbing from NYC it sounds like you definitely have a leak .

It can be plumbed to do that but I suggest against it.

Keep enough savings for several months of problems with rent and access to money in case something big happens (eg new roof, plumbing problems, appliances in two units break at the same time).

Any broken pipes have to be replaced but you should go through the additional expense of upgrading the entire plumbing system to pex because it is more resilient in cold temperatures.I know politicians and media claim the earth is heating, but I am expecting more cold weather in the next ten years and people should prepare for it.

I understand that science has not eradicated disease - rather it has controlled it through various methods through the ages like indoor plumbing and vaccines.  

Emerald Plumbing does a lot of work for local investors and are great with repipes from polybutylene if that is what you are in need of.

For our home this spring, and the future, I would love any contacts or recommendations for: interior and exterior painting, kitchen design, handyman, plumbing, electrical, chimney repair/mason Thanks so much to the community!

The standard in Chicago is typically a 1" lead service, which is sized large good enough to serve a 3.5 bath w/ kitchen and laundry (according to the IL Plumbing Code).