Within this, he will let me know of any structural defects (red flags), electrical, plumbing, roof, etc issues.

But now that I am looking over the lease documents and there is this section already in there: "All personal property placed in the leased premises, or in any other part of the building, or any place appurtenant thereto, or inany vehicle on or about the premises or on any parking facility maintained by Lessor for Lessee shall be at the sole risk of Lesseeor the parties owning same, and Lessor shall in no event be liable for the loss of property of any kind, which may be lost orstolen, damaged or destroyed by fire, water, steam, defective refrigeration, or otherwise, while on the leased premises or in anystorage spaces in the building.

Further, you're buying it subject to any existing liens and encumbrances, and subject to any title defects past, present or future.

Under California Civil Code Section 1710.2, if someone dies on the property, it's a material defect – but only if the death occurred within three years of the date you make an offer to purchase or rent the home.

If you believe him when he says he can cure the defects then go ahead, if it turns into a debate and you get excuses but no solutions, cancel and find a better painter.

As a buyers agent, it's my job to help you accomplish your goals, such as getting a good deal, protection from buying a property that has a material defect, clear title, loss of earnest money, etc.

Just because it is near the end of its projected useful life is not a "defect".  

No bank or lender is going to shell out money for a property with major defects (structural, roofing issues, mold, fire damage, termites, etc, etc).

Obviously, they failed to disclose this defect!

The contract says the Seller (in this case is the bank) at closing is responsible for delivering to the Closing Agent "The transfer deed warranting against title defects arising by, through or under Seller", and the contract does sound like this is an REO.