My thoughts are two fold...
1) The starter is a 6 volt starter.
First off it draws more current than a 12 volt starter and may be causing the biggest problems in starting and that is why you had to double up on batteries to jump it.
If you really want this tractor you should consider either looking for a 12 volt version of the starter or find someone able to perform miracles and transform the starter to 12 volts.
2) Being the wiring.
A) The "I" terminal in the solenoid is to give a 12 volt shot to the coil when starting only to get things goings, your wiring has a resistor in line. If your coils/points/condenser is converted to 12 volts then it isn't getting start voltage. If the ignition components are still 6 volts and you are using 12 volts,on them, then they won't last long and may even cause starting problems.
I usually have seen the resistors in the main coil hot not the solenoid feed.
B) the solenoid, make sure there is bare metal and a good conductive paste between the solienoid and the mounting bracket for the solenoid, make sure it is tight. The mounting bracket is the ground for the solenoid.
C) The starter connections, eliminate the brass strip between the solenoid wire and the start post, too many connections. Also, as LD1 and I have suggested run the extra ground wire to one of the starter mounting bolts to give the starter a better path to battery ground and not depend on all of the poor connection through the chassis and other components.
Second thought... That brass strip may be an older attempt at a 6 volt shunt, it may be needed.
I think your biggest problem is the starter, if 6 volts it is taking a beating every time you use it. You need to make sure it is a 12 volt setup. Clean up the wiring, eliminate all of the extra connections and check the purpose of the resistor on the "I" leg of the solenoid.
Remember one thing, I am not an automotive Electrican, I am just throwing out ideas some of which may be thrown right out the window but they are things that have worked in the past on older hot rods.
Good luck, take your time, clean things up, check things out.