Someone screwed up, plain and simple.....
The large hole is for the factory mast raising system, and there should be a nylon bushing attached to the opposite side for the gin pole to set in. That is NOT the hole for the mast wiring. There should be a small hole above the large hole for the mast light wiring to exit, and every MK-II would have a hole for the mast light wiring, right from the factory. First indication someone screwed up is that black wiring wrap is someone's doing's, it didn't come from the factory like that.
Did the boat come with the factory mast raising system?, how about a stainless steel mast crutch? How about 5' long stainless steel cables with pelican hooks on one end and T-fittings on the other end? If it has a stainless steel mast crutch, it probably at one time had the factory mast raising system.
It almost looks like someone tried to raise the mast with the gin pole and the nylon bushing was missing, or they didn't know how to correctly install the gin pole and missed the bushing. The gin pole has a slight angle built into it at the base,(this gives it a slight upward tilt so there is room for the block and tackle when raised), and if not installed correctly, or the bushing is missing, or broken, I could see this as being the result. Somehow some serious prying was done.
The photos show my mast base after years and countless mast raisings and lowerings. Also, if you look at the end of the gin pole, you can see the slight angle I was talking about. It's not a straight shot.
In my opinion, yes it is bad, and it needs to be repaired properly by an experienced aluminum welder. Lot's of stress at the bottom of the mast when it's being raised, and that crack weakens the area.
Is the "stop crack" hole in line with the center of the large hole? In my opinion,(yup, got a lot of opinions), it appears to be in line with the center of the gin-pole hole, and was drilled by the factory, not the marina "expert". Also I smell a rat, "if" the expert did in fact drill the hole,

, going back to my aircraft airframe mechanic training, you don't need that big of a hole to stop a crack. Again, in my opinion, sounds like BS to me.... :naughty:
How could the previous owner have not know this?

This was caused by a serious screw up, and somebody knew it happened. From the photo, it's obvious there was some severe prying going on for whatever reason, the damaged metal says that. Somebody, i.e. previous owner, or the marina "expert" is full of it in my opinion. If the previous owner will sign a letter stating this damage was not there when the boat was put away for the season, then the marina would seem to be responsible.
Might be time for a small claims filing. Maybe the threat of a lawsuit will get someone talking.
Don