hobie mirage

Yes. Yes you will.

Another thing you will have to consider is the fact that you are probably going to have to be using at least 8 oz. of weight to be fishing that deep, probably more. You'll need to try and stay as vertical as possible and the diameter of your hand line is going to be working against you in that regard.

that part should be ok. pain in the arse yes, but manageable. I've been working out allot with 4oz curls it will suck, but it's doable.

You just might be the guy that needs to try something for me when you get that pissed off doormat up to your kayak. 

Take a spray bottle of Vodka, or Rum out there with ya, and when you have the beast at your yak, spray a liberal amount of liquor into/onto it's gills.  If I'm right it should get it drunk real quick.  Then you got to hope he's a sleepy or happy drunk, and not angry drunk.  Then tie his mouth to his tail so he can't beat the shizzle out of you.   

It's going to be a sh*t tornadoe no matter how I go about it. This is what I spend my free time pondering. I'll work it out to a reasonable level of "risk" and "sanity"

Now that's what I'm paying to see....

I have caught tons of fish (tuna) with a hand line and even a few rockfish/lings just for fun.  It takes most of the fight and "fun" out of the equation. The "hauling up a truck tire" comment is very accurate.  You can hand over hand a 30lb albie into the boat without even slowing the boat down.  We called them "meat lines", if you wanted a battle and a test of skill you used a rod and reel, if you wanted to just fill the freezer you ran 5-7 meat lines out the back.

That said if its your thing, I would recommend putting knots in your main line every 10ft or so. It gives you something to pull against and helps a bunch. Not needed with small fish like lings etc but with bigger fish like tuna and I can imagine halibut, you'll need them.  I would also make a way to snap another length of line, with a float on the end, onto the back end of the hand line incase you hookup with a large butt.