Ok...well, with that being said...
When you richen up the jetting, you're putting more gas/oil in the cylinder.
An old school trick to check ring wear is to do a compression test on a motor and then add a few drops of oil to each cylinder, and check it again.
What the oil does is help worn rings seal better. (Obviously, once the motor fires and runs for a few it'll burn that extra oil off)
So...based on what you said about the blow by, it is probably either time for a set of rings and a hone or a bore and new pistons/rings.
Here's my honest opinion, if it has blow by...and it's 14 years old, bore them fresh and put a new top end on.
At 14 years old, it doesn't owe you anything. Even if the rings are sticking to the pistons a little due to carbon/wear, etc.
You have to take the top end off to clean, measure and check things.
At that point...why not freshen it up?