Sounds like a marginal start condition. In the water you have an immediate load on the impeller. On the trailer 9or lift the rear end) and you don't. But a ski that is that fussy has something wrong. Probably weak spark or slow cranking speed. Try trimming a 1/4 inch off your spark wires to get a clean connection at the boot. does it run OK normally... because a sheared flywheel key will shift the timing a bit... makes for hard starting, but it probably won't run so well under full power either. I recommend a primer using real pre-mix gas as a starter helper, rather than starting fluid that has no lubrication qualities. Is the choke functioning?... does it really close?.
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