I honestly didnt realize it had to be clipped in a particular direction. The bottom of the U was following the chain movement. (should it have been the other way?)
Regardless, between the two breaks I no longer have any more master link clips - and will likely just order the chain Johnny recommended
1) engine a bit loose and starting to lean to the left
2) rear sprocket a bit off in the up/down direction & chain tensioned at the loose spot (when it gets to the tight spot it'll snap)
3) tensioner not feeding the chain so that it is centered on the rear sprocket (making it ride up onto the tops of the teeth) - can be cause by tensioner out of line, or by sprocket being off in the left/right direction
So chain issue is resolved - switched to the K910 KMC KoolChain, and have attached both ends directly (no master link), and it looks like its holding up amazingly.
However, the engine continues to cut out. I believe this is due to the fuel filter--the gas is only filling up around half way, as such the fuel isn't making to the carb consistently (if at all)