Re: Slow leak from motor bolt on transom
It looks to me like there's already been some attempt to stop water intrusion w/ caulk/sealant of some type behind both bolts you posted.
As already mentioned I too suspect that the water at the thru bolt is the tip of the iceberg.
You can cut the bolt head or nut off, tap the bolt thru the hole & take it to get 4 new sets. If you're pulling them to inspect the interior of the hole (which is IMPORTANT), apply sealant & reinstall, and you have to go to HD/Lowes to get at least 1 bolt/washers/nut setup anyway, 3 more won't be cost prohibitive. It'd be cheap insurance.
Doing them 1 at a time may be possible. Depends on what you find when you pull the 1 rusted~frozen 1.
Let's get these pix over here where their easy to see:
Typically you'd use a wrench on the outside bolt head & the inside nut to loosen a thru bolt & nut. They both just spin?
The outside nut on the boat has some rust and could probably use replacing. I'm worried if I force the bolt off, I don't want to make it worse. And I'm not entirely positive a can get the thing off. The nut and bolt head keep spinning but not loosening.
So the bolt is sheered off in between somewhere?
Hit the bolt threads w/ a wire brush to clean out the threads (don't damage the threads).
Tap the bolt end at the nut w/ a metal hammer, liberally apply the penetrating lube of your choice (WD40 wouldn't be my 1st choice, but most people have some) to the nut as best as you can to both sides of the nut, tap the bolt again a few times. Just enough to get a vibration thru the bolt,
NOT enough to damage the threads on the end. Repeat several times thru out the day(s).
EDIT: redacted by request
A few cycles of tapping & lube might free up the nut enough to loosen it.
I suspect that if you pull that lower port thru bolt & carefully inspect the condition of the transom, you'll find that you should probably pull the motor off, and do a much more thorough inspection of the entire transom.
BTW: What's that washer looking plug above the lower bilge drain plug socket in the last pix I posted?