My first plane, a cherokee 140 had damage in 1967 (hit power lines), three months after it was delivered. To make matters worse, there were no records between 1967 and 1984. By the time I bought it in 2000, it had been completely rebuilt by the prior owner who had immaculate records from the time he acquired it in 1984. It was a risk, but the plane was in great shape, and it had been flying for 33 years since the accident. I bought it anyway and was extremely happy that I did. When I sold it, lots of people asked about damage history I don't believe it was a major factor in their decision to buy or not to buy.
My 152 was totaled for hail damage, but the owner elected to use the insurance proceeds for a new interior and paint job. The dimples on the tops of the wings are barely noticable and I think he made the right decision in not reskinning. I surely have never regretted the purchase.
