What is Reddit's opinion of eBoot Plastic Waterproof Adjustable 3.5-13mm Cable Glands Joints, PG7, PG9, PG11, PG13.5, PG16, Pack of 20?

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That is exactly what they are fine sir. I bought an assortment to avoid buying wrong size vs cables.. eBoot Plastic Waterproof Adjustable 3.5-13mm Cable Glands Joints, PG7, PG9, PG11, PG13.5, PG16, Pack of 20 https://www.amazon.com/dp/B01GJ03AUQ/ref=cm_sw_r_cp_api_glt_i_TMTE4D2VY0J689QFHD93?_encoding=UTF8&psc=1

If you really want it to be water tight you could get some of the compression seal nipple plugs and a water tight box and build an enclosure for them that way. Basically you'll just leave the cable plugged in on the terminal side and only plug unplug the ipad side.

What do you mean by helm guard?

eBoot Plastic Waterproof Adjustable 3.5-13mm Cable Glands Joints, PG7, PG9, PG11, PG13.5, PG16, Pack of 20 https://www.amazon.com/dp/B01GJ03AUQ/ref=cm_sw_r_cp_api_glt_fabc_BBDHZPS5XDE9AV054X7V?_encoding=UTF8&psc=1

Cord grip, something like this

https://www.amazon.com/eBoot-Plastic-Waterproof-Adjustable-3-5/dp/B01GJ03AUQ/ref=sr_1_1?ie=UTF8&qid=1488591208&sr=8-1&keywords=cord+grip