Richard and Adelaide Lewis (FS 367 - Chin Up) has a simple solution to the fouling mainsheet problem.  They use two plastic container lids and faces them together.   Drilling a hole through them and slips the shaft from the lower mainsheet block through.  In their message they indicated that these will last about one sailing season before the plastic begins to disintegrates.  

Bill Ross, long time Scot sailor from Lake Norman, made these comments pertaining to the fouling main problem.  "When in the process of jibing I take hold of the mainsheet at the boom block and just as the boom starts to move across the boat, I give a sharp jerk to the sheet.  This takes up the slack and the mainsheet moves across the rudder nicely.  I have never had it hang up on me since I started doing this.  I use a 2:1 sheet to minimize the excess line to handle, and in all conditions.  A 3:1 arrangement may not work as well because there will be lots more line to take in.

Thank you Bill, give these ideas a try.  Perhaps one will make your sailing more enjoyable and remove one thing that you have to worry about.

Richard Lewis (Flying Scot 367 - Chin Up) provided this suggestion concerning tiller extensions.

I have the original wood extension that, probably, came with the tiller (circa 1962) with only a single bolt going through both the tiller and tiller extension.  There was nothing to secure the extension when it was not in use, so my wife fabricated a double sided strip of velcro and I put a single staple in place under the tiller to keep the velcro from dropping off when the extension is in use.  When the extension is not in use, the velcro holds it to the tiller, nice and secure.