I was wondering if you did a compression test on it to see if there is any compression in that cylinder at all?
Do you see any broken inner springs in the head in #3 ?
I would do that before taking the head off which would be the next move.
Once that is off you can check the condition of your valves, Check how it seats......
Look in the cylinders and see if there is any scoring or digs, check the condition of the top of the piston....
You are already into a new set of gaskets so don't be shy , next you remove the jugs inspect everything for unusual wear,scoring, hotspots from blow by...if you can find that you're on . don't spin the rings around like we always do , just inspect it carefully for damage and installation correctness. (Not upside down) Check wrist pin and piston for slop. Measure the bore for round all over the cylinder in question, look for slop on the rod , just wiggle it sideways.
This isn't that hard, you and your son can do it. Get the manual for your machine so you have the particulars, both of you read it, take your time, don't rush it, this is a learning experience, Enjoy the time with each other it goes by so fast.
Let's hear what you find, take plenty of pics please, and most of all have fun!