Before you get yourself all worked up over nothing...
Based on the pictures this looks like superficial cracking in the gel coat. Nothing more. The area that had been previously repaired.... well no offense but just looking at how that was done do you really think whoever did that knew what they were doing? Looks like a 2 year slapped that on over a problem (there I fixed it) and is clearly a sorry excuse for a repair. It likely cracked again because of that.
Fiberglass as a general rule doesn't just crack like that, if you think about it, what is fiberglass? Layered resin filled fabric typically in multiple overlapping directions which is exceptionally strong and can't just crack unless there is some sort of massive impact. Even at that it sort of tears versus cracks. In fact much like a vintage corvette (all fiberglass body) the paint on those notoriously cracks over time in the same way gel coat can.
IF there was a transom problem where it has imbedded wood and it was compromised this is to me the last place you'd see a problem as there is far more stress in and around the actual stern drive housing. Also if there was that much compromise I'd think the damage inflicted would be quick and catastrophic.
I've looked at plenty of used boats, and see this sort of thing all the time with age comes superficial cracks like this.
The only thing I would be concerned about is if the boat sits in the water which it clearly does, water getting between the gelcoat and underlying structural glass which would cause blistering. This was a very common problem in and around the time of when your boat was manufactured across all brands. Modern day building techniques and materials have all but eliminated this problem.
Just my 2 cents.
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