Gonna start by saying the ignition key has wore down to where i believe a pocket knife could start this thing. And I think that could be some of my problems but looking for a little confirmation.

Also I know the PO i bought it from didn't do any electrical work on it, but I also know he didn't buy it new.

1st, start it in park and leave it there and the starter will try and engage again after a few min on an intermittent basis.

2nd, put it in park while it is running and it will stall to the point of almost dying. leave it in park long enough and the starter will try and engage.

I'll take any advice. Work around has been to quickly engage to a gear after it starts and shut it off in gear then put it in park.

 

Does it sound like flywheel mechanically grabs the starter gear and turns with it, OR

Starter motor electrically turns, and engages flywheel as if ign switch were put in Start position?

Try this:
While idling as above, disconnect spade connector from starter solenoid and see if symptoms persist. Then report back.