The house needs a roof and the existing roof is very old asphalt over cedar shake so according to the roofers they need to completely remove everything down to the rafters and install 5/8th inch plywood then reroof from there (one estimate so far came in at $31k for that).  

Snow, meanwhile, is minimal—the city gets an average of an inch or two of snow per year.

The pipe bursting caused extensive water damage to the second and first floors and about 4 inches of flooding in the basement. 

REI Central meetups in CHS would be a good place to start if you don't already attend.

Dig a spot in basement that could accommodate a sump pump .Even if you half to cut through 4-7 inches of concrete.

I would have paid another experienced local investor (an unbiased party not having anything to do with the sale of the home or selling me services) to do a thorough video tour of every inch of the house before submitting an offer. 

What the fools didn't realize that the greedy managers of those Senior Living Residences would prevent millions of seniors who are financially unable and unprepared to afford the small condo-sized unit residences + vehemently UNWILLING to move into such residences instead preferring to remain in their beloved homes where they lovingly raised & cared for their spouse & children and where they know every single INCH of their current home!

I had 1 contractor come by today and quoted me a French drain system, as well as raising the basement floor up 6 inches, with 3 sump pump's for a price tag of $16K, not including the repairs to the walls. 

One last tip, make sure the base boards upstairs are not touching the floor, even just 1/8 inch gap is good.  

You sink in about 2 inches when standing in it.