It would not be a deal breaker in my view. You say the
boat has been well cared for. That is a good start, and a good indication of what you are looking at.
The
deck chip should be no issue - appears to be a void in the lay-up under the
gelcoat.
The stern damage does not appear to be great, but of course needs to be checked properly.
The impact will have - apart from damaging the
gelcoat, caused some separation of the glass mat, from the resin. Probably by a very small amount, but even if it penetrates more than is initially apparent, it is no big deal. There is no
core down there - just resin and glass mat.
It could be repaired in the
water - dig out the damage, check further, wash out well to remove
salt, blow dry with heat gun, leave under a 'bandage' of paper towel and duct tape to protect from wave slap or rain.
Check next day to see if towel is dry - if not, more drying required.
Once fully dry, impregnate mat with new resin, build up, fair off, top coat of waxed gelcoat, fair, and polish.
Done