So far as I can see it's not coming out of the prop. Looks more like it's escaping past the muffs. Show some pics while running at the muffs
The thermostat housing on the 888 has it's own issue and why it was changed many times
I have 2 Garmin and do like them, they only look forward. Got it after sleeping Cop gave me a ticket
This ONE
and I turned off interior sound and GPS speed
KY property line comes up to the shore line of IN, plus it's a Federal interstate water way therefore USCG has authority
IN has all kinds of fees and the link explains a few of them
https://www.in.gov/dnr/state-parks/rates-and-fees/boating-fees-and-lake-permits/
No, no kind of cranking will induce water in the cylinders
No
Kind of, sort of
Intake crack can induce water into oil, but will not be slow
My opinion
You need a Mechanic to look it over, the process of DIY is a bit beyond the current understanding right now
It's most likely fuel related, either not enough or to much.
When it stumbles look down throat of carb to see if it appears to be flooding. If no flooding, need a fuel pressure gauge and Tee fitting. Measure pressure at the carb