I'd try some heat from a heat gun to soften up the sealant and instead of prying or driving wedges or chisels around the edges, like you might do on a fin or strut,  use a slide hammer  through the rudder port to get some good downward force.

It's probably pretty tight in the hole.

It's most likely the same sealant as your strut if they were both original and the strut came off easily from the sounds of it.

The strut was off before I even knew it. The fins took very small amount of convincing.

I think plan B will be just goop the bolts and put them back in, but obviously I'd rather reseal the entire piece since I know it's leaking.

The shims start at a very sharp point like a chisel.  They widen to about 3/8" at the end of the 10" run.

Tap the sharp pointed shim into the gap between your hull and the rudder port.  Add another shim next to that and just keep adding shims.  Tap each in a little at a time going from one to another slowly increasing the pressure to split the rudder housing away from the hull.   My boat had 5200, the hard stuff, and the shims popped it right off.  It worked for me and the wood did not damage the fiberglass.

Once the port is removed I took a very sharp automotive gasket scraper and cleaned the rest of the old 5200 off the fiber glass to prepare for the new install.

My company has several "brown water" work boats.  On board, I've seen cases of 5200 in the parts room.

JQ

Kinda like your strut bearing the other day or the fuel gauge replacement Rick.

I guess looking at your different recent threads on the strut bearing and the fuel level sender, I wonder why you seemed to go to the extra effort to slide the strut past the rudder and ask about level gauge removal and install without removing the tank if you were gonna remove the tank anyways to remove the rudder and port?

I think I'll just sit back and observe the upcoming what's the best sealer/adhesive discussion 

Residual 4200 and 5200 come off thin as tissue with a razor blade as soon as you spray the brake kleen.

 

My dumb questions usually are centered around what makes the most sense for me. Can I accomplish the task in question successfully. What order is best to do these things... If I have to prioritize and leave things until after FL, how can I do that... For instance, I was very grateful to know that I could do the strut bearing without removing the coupling from the prop shaft. Despite the great idea on here to remove it, I pictured that as a really possibility of a crap show on something that had not been apart since 1997.

I truly appreciate the wealth of knowledge you guys have and are willing to share. Thanks!

Been doing some reading elsewhere

U seem to have quite a project going on, maybe finished ?

Ford COE that was

Old

Rusty and 

Dilapidated

 I'll bet people would be interested in hearing a little about what I'd call a huge undertaking 

PS Nice boat in the background 

I keep telling him to install a Diesel so he will have more power and MPG.  Those old cab overs have really taken off, they make beautiful and rare projects that people remember.

My buddy Carnac seems to Rick's is a crossbreed of some Chrysler, Ford and Chevy parts (and probably some other brands too) with a fair amount of engineering and fabrication involved

I see what you did with the truck's name!

McD, does your buddy have a build thread somewhere?

Carnac is correct... Ford cab, 2002 Ram 1500 frame and axles, 1999 Corvette LS1 under the Peterbilt sleeper, some Studebaker parts, some Isuzu parts, lots of figuring stuff out...

32 pages of build thread live here if anyone has a few days to kill....

32 pages of good reading, but I think unless you're a member there, the link won't work 

Easy to join

They seem to have had some site issues over the years that affected lots of the pictures in your thread, but still a great read and an amazing, difficult project

I have thoroughly enjoyed the COE build and really wouldn't trade any of it. But if I had it to do again, I think I might look harder for a less rotted starting point. I learned A LOT fixing it which was fun, but it was a HUGE task.

This is probably my favorite picture from a car show that my buddy was able to catch...

37 Chevy - since sold

Drag truck - before

Drag truck - after

Roadster - before

If you use a heat gun, a hammer or slide hammer, a screwdriver, a chisel and some shingles (shims), a pipe, and a razor knife you'll probably get it out 

Could be, I am sure there is not a real tight specification for that at the factory, but mine just had one wire through both the tiller clamp bolt and the top bolt.

Boat Life, 3M, some other equivalent brand, bubble gum ?  

I miss the oil drain hose on the pan's plug that the 1987 had...