Home Inspection Reveals Material Deficiency!!!

[Matt Romano]

To material deficiency, or to not material deficiency. That is the big question.  But really thats just the subject title.  I'm pretty sure I have a decent understanding of what is and whats not considered to be material deficiencies. So I had a home inspection done on my first purchase ever. And I am just going to bullet point everything here that was noted with some type of recommendation by the inspector: 

-repair / seal walkway / (cracked concrete)

-cracked retaining wall

-some cracks in foundation (house was built in 1930)

-few areas of rot around window trim***

-1 piece of vinyl siding missing

-garage structure very questionable, including roof, and signs of previous (maybe even current) pest activity***

-front gutter brackets not under shingles like they should be*** 

-crack in chimney

-some broken basement windows

-doors throughout the house that don't close / latch as they should 

-2 visible signs of knob and tube wiring 

-lack of support to beam in basement*** 

-cast iron water pipes in basement rotted (should be replaced with PVC)***

-some leaky faucets throughout 

May seem like a lot, but honestly I didn't think it was too bad of a list considering the age of the house. I starred (***) the things that I would consider to be most important and hope to get a price reduction so I can address said issues. This is going to be my first purchase (owner occupied house hack), and its currently under contract.  Closing date is supposed to be next Friday, but I honestly feel that its super rushed to meet that.  I am having a contractor get in there on Monday afternoon to quote me repair of at least the items I starred.  But I guess my question for you veterans is: how do you usually deal with contingencies. Obviously I feel like I'm being picker than most because I will be living there myself, and I want my first investment property to be a sound one with as little headaches as possible (surprise surprise, right?). But how far do you usually go with addressing issues that come back from home inspection report,  Would love ANY and ALL feedback.  Thank you so much in advance!

-Matt