I cringe (like ice water on a chipped tooth) when I think about it, it's just me. I consider that a last resort. Probably from a lack of experience with fiberglass.

I will definitely not recommend removing the skin as the first and only option, However but if you have a partial rotten transom like this and mine, removing the skin is the only way to go.
It is VERY IMPORTANT that all traces of wood be completely removed since the new transom needs to glue it self to the bottom of the Boat
This part of the Transom to me this is the foundation and the strongest part of the Transom.
Please be sure to use Acetone as the final clean up agent since it removes all traces of contamination and old mold from the surface then brush fresh resin on the inside area let it dry or to a tack then pour !
Use thin roller brush for acetone and resin.

"Am I just being a pansy and I need to just keep chipping away at it?"
Your not. Do your drill extensions reach the entire depth of the transom? If so, don't force them, let them do the work. Drill as much as you can in an area then use "whatever means possible" to loosen the wood chips/fibers. It will take some time. The flat blade I used acted like an ax and I was able to get the wood out in little slivers. Not efficient, but it worked. I had some sore arms when it was all over but I bottemed out on fiberglass across the entire width of transom.
Maury

Dont remove the outer skin. It will never be as strong.

Not if its done correctly, On mine I layer multiple layers of mat from the inside across the cutout sealing and adding extra strength and thickness to the skin in such a way it appears and tested stronger than the original. Hey if mine ever cracks or shows any issues I stand corrected.
On the morning of the pour I again coated the insides with resin let dry then pour the Arjay.
An old timer did a test on my Transom before and after my stress testing and told me there is zero flex on my transom.
All I am saying is if your transom is completely rotten then don't remove the skin, if you have a one half rotten and solid at the bottom then remove the skin..

I still think that taking the boat apart is the best way to replace the transom on a v20. The hardest part is figuring out how to hoist the inner section out of the hull. We had mine apart in a day and this gives you acces to every thing below the flooring like the stringers. I wish I had replaced the flooring at the same time when I had access to the bottom of the floor.

[quote=nymack66;136768]
An old timer did a test on my Transom before and after my stress testing and told me there is zero flex on my transom.
quote]

What's the procedure for testing for flex? I have pushed and pulled on mine and all seems stiff but I always wondered if I needed to do a better inspection....(although I'm a little scared!!!)

I just got done removing the wood from mine and as mauryc said it is brutal, but it can be done. I would say I have gotten all the wood I can out probably around 90 to 95 percent and the whole bottom is down to the fiberglass all the way across. I do have some very thin wood left on the sides in places but it just won't come off so it is staying. I was a bit conservative with the chainsaw and chiseled most of the bottom out which seemed like it took forever but I got there. Keep chipping away.

[QUOTE=RWilson2526;136791]First I tilt the engine all the way up and lock it in place, with me pulling on the prop he was visually check both the outside and inside for movements or flex. Note (I did this before the new transom) and yes it did flex !
On the lake he use tow pieces of 2 x4 and made a mark on the floor of the Boat , I did some 360 and WOT etc, all seems well and no flex.

For this stage use a sharp wood chisel and attach duct tape it to a pipe this works , Also it did rain and fill up my project when I was working on it low and behold it seem a lot easer the next weekend when I finished it.
The wood came off the skin with no effort !