You can make any offer you want to a seller of a used house. 4 years ago when things were selling in a couple days, I offered $60k less from asking price and they countered to $50k less. Now, with houses on the market for months (used houses now), depending on what the owner paid for the house, how desperate they are, and how much I wanted to spend or how bad I want the house, you might pay full price or offer hundreds of thousands off the listing price. I would always get an inspection and have a clause to back out of deal or have seller fix the repairs needed.
As for roofs older than 15 years old, yes, an insurance company can refuse covering you unless you get a new roof. I’ve never encountered this in other states, but in Florida, insurance companies require this.
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