I'm not familiar with the specifics of rigging on a skerry but you should not be sheeting from the boom end of the line. You can do a couple things to improve your set up. Add mechanical advantage and or a cam lock block to lock the sheet in place after you sheet in. Your sheet should start at the block attached your seat then to the boom block then back to the seat block, through a cam lock and into your hand. That way you are always sheeting from the same place, not from the boom!. There are lots of ways to accomplish this. Maybe some of the Skerry guys will weigh in some other ideas.

Hi nighduckman2!

This is how I rigged my Skerry, like McCarty J has mentioned: I clipped a block to the seat with a carabiner and lashed the other to the boom as per plans. The mainsheet is tied to the seat block, passes through the boom block (back to front), passes through the seat block (front to back). 

In a small boat like this, it's generally a good idea to always hold the mainsheet. If you're solo and fall overboard, the boat doesn't run away from you, or you can let it go quickly in a sudden gust. However, many people have added cleats to help out (myself included). Never ever ever tie the sheet to yourself.

I added CLAM cleats to the rails. It's not the prettiest option, but it gets it done. I've seen someone modify the seat to hold a fixed CAM cleat. It's also possible to have (at the seat) a block with a cam cleat attached to it. I think the last option is best, but I haven't tried it on a Skerry.

Another option is to increase the mechanical advantage by having double blocks. The mainsheet is thread through in the same pattern, but I believe you will have to pull twice the distance to get the same sheeting angle. This means a lot of rope at your feet to get tangled up in.

Gloves are a cheap investment that pays dividends. I use inexpensive cycling gloves.

Have fun!

Jean.