even though it has on off switch on cap, it can quit working sealing the tank and not allowing gravity to do its job properly.
hard to tell from posts but is the engine always cold when this happens or is engine hot or both. somethimes electrical components can start acting funny when hot. mainly generator inside engine. also heard ignition coils can act funny like you are saying. it sounds like you know when it wont start the plug is wet, so its either flooding or loosing spark. i would say next time it wont start, push start it as you say you do. if it still wont start immediately pull plug and check for spark, if no spark then check for wet plug. if it is wet quickly dry it or use another plug and check for spark again. if it sparks, flooding is only your problem, if no spark look at generator or coil.
also check your harness for bare wires or bad connections. could be intermittently grounding or loosing connection
Trikes: All Honda: 84 250r, 85 86 and 87 250sx, 84 and 85 125m, 79 82 84 and 85 110's, 73 us 90 and 77 atc90, 75 atc70
Cycles: Honda: 71 cb100, 78 cb750 coming soon cb750 trike. Yamaha: 67 yds 3 (250cc, 2cyl, 2 stroke), 82 750 SECA
Other toys: Chenoweth VW sandrail dune buggy, old race go kart, racing mower, 76 Arctic Cat Pantera 440 snowmobile
KEEP IT ON ALL 3 OR AT LEAST 2 AT A TIME