My contractor said we might have to pour some concrete down there but we won’t know the extent of the fix until he opens up the floor.

She is also ok with pouring the concrete in the areas of the driveway that desperately need them. 

Regarding buying a single family and converting it to multifamily, not all properties can be converted into multi family due to Building Code, Zoning and ADA reasons.

I would be curious on this because that would help me make a more concrete recommendation.

That said a friend who has multiple properties told me you can't have a range, so you can have a cooktop and microwave/convection oven and be code-compliant. 

Hi David,This may be too late for you, but this is a common issue when laying tile over top of concrete if not done properly. 

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It requires about $7.7k in concrete and dirt removal and replacement to prevent water from entering the house (as well as fixing the windows and drain pipes).

She wanted to demo basement wall, dig out 500 sf of crawl space and put egress where concrete patio it. 

Been searching around for an answer to this, but found nothing concrete.