your repair costs are light given the work you described....Just for reference a 2 car garage with concrete is about $12K in Chicago I would look into the rents in the neighborhood to make sure you can offload this.

If I were holding the property for an unknown period, I might put in a temp fix with some 4x4s on a substantial concrete pad next to the old column.

Bill Gulley Well when i think of container homes , i get a picture in my head of more customized kind, multiple container welded together, more like a hybrid, part container part normal architecture (concrete ).

You definitely need some more concrete information to back up the prior owners rent claims. 

Looking for an investor friendly real estate agent within the inner loop including for example South Union, areas surrounding Medical Center, East Downtown (closer to concrete solos), North Downtown (near light rail), the Heights and similar who is familiar with BRRRRing, buy and hold, small multifamily (if available) and small - medium sized lots.

They countered and requested a lot of repairs which included leveling the back yard and tearing up the concrete basement to replace outdated pipes.

Piles of dirt 5 ft high and just as wide in pretty much every room and concrete dust everywhere else.

Location: downtown Truro, 10min walking distance to business district.Rent roll(verified with tenants): 1st unit, largest: $1195 (tenant pay cable)2nd unit: $1100 (tenant pay cable)3rd unit: $ 700 (tenant pay heat, power, cable)so generally, first two units, heat, power, and internet are all included.Expenses anual:Insurance: $2900, Heating $5022, Power: $1904, Tax $4348, Water/Sewage: $640, Snow/Garbage: $172Pros: Great location, good zoning, ready to move in condition, two level garage but pretty shabby.Concerns: There are some water leaks in the foundation(stone and concrete), there are two quarter-thick cracks near the foundation(the bricks are tilting and shifting a bit), age.Given all above, are the listing price too high ?

Does it need flatwork/concrete?

If there is hardwood under the current carpet, I'd recommend removing the carpet and sanding and/or polishing the wood.