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Offering way below list- super nice seller!

Has anyone ever had an extremely low ball offer accepted? For context, we found a house that suits all our needs (home itself). It has slightly less land than we would like and it sits up on a hill and there are some steep drop offs (kids could fall down and get hurt, nothing that would kill ya though).

Anyways, house is listed at $600k. Started at $800k but dropped $100k and than $50k 2x. The house needs all new windows (about 30 windows), new kitchen & utility room flooring (tile is broken in lots of parts, roof and HVAC are original (18 years old), new exterior doors (4 french, 1 front), and then we would want new cabinets, a fence installed, and some wall paper removal/paint.

Our agent ran some report and showed that comps with similar size (3600sqft) it should be between $435k-$520k. We were thinking of offering $450k but, we also met the seller and he is an extremely wonderful person. So much that we are afraid to offend him. He wants the house sold so bad because he lives further away and said he never wanted his home to start at $800k.

Anyways, has anyone ever had success with an offer $25% below list? Have you ever written a letter to the seller explaining your why and apologizing in advance if they are offended? We are torn on walking away since it isn't 100% what we want in terms of land and the seller is so sweet, or just going for it since the house itself checks our boxes

submitted by /u/Content-Duck-7608
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source https://www.reddit.com/r/RealEstate/comments/1g2055o/offering_way_below_list_super_nice_seller/
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