Is this a sign of transom problems?.

[mushman]

Hello, I just found this site, and I wish I had many years ago.
I've had my 1986 steplift since 98' and love the boat.It had a sea drive which was replaced with 24" Armstrong marine bracket(size recommended by the mechanic doing the job), and 1986 150 hp evinrude, had it done in 2001.
Here's my question.I have drilled into the transon a few times for my transducer,speed, cables and what not.
The wood inside seems soft, when I get through the gel coat the drill bit just goes right through the plywood.
It comes out clean almost wet looking(dark brown) ,but dry.
The cap covers the whole transom so I really cant go down into the transom I can only get it from the sides.
I've stepped on my bracket with the engine on and really don't notice any flex.Will the gelcoat show stress cracks before the whole thing goes?.I haven't seen any as of yet.
I live on long island, nassau county, are there any recommended shops to do this type of repair if it is needed?.
Here's a few pics,the cables have clamshells over them, they were just off at the time.