I Would avoid hot glue as total fool proof water insulator. When cooled down it isn’t elastic enough to maintain full water resistance in changing temperatures. On day to day basis I use it for the same reason. It’s stupidly easy to remove from connections on the prototype phase. However not to say it’s completely useless. As you mentioned adding it to connected connector prevents connectors from accidentally disconnecting from vibration.
The route I went is enclosure lids held by screws and a generous amount of silicone, every time you open you have to cut it, clean everything and apply again. For wires the only solution in no wires going through the enclosure, only connectors glue really well and fully covered with silicone from the inside
Have a lot of pictures here
Gathering Storm | Trampa HolyPro | Dual 6355 | 10S5P | VESC 6 | Submersible
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Back in the day when I used to race RC cars we used a product called “Parafilm” you can stretch it and wrap it around electronics such as receivers and ESCs and it worked remarkably well at keeping out water and fuel.
I found another similar product recently when I was installing an external WiFi antenna on my house. This stuff is thicker and more robust and it is called “Self-Fusing Silicone Sealing Tape”. The brand I purchased is “proxicast” and it stretches quite a bit and then only sticks to itself but not other surfaces. It is typically used where two cable connectors are joined and are going to be exposed to the outside elements. I am thinking this would woprk well for getting a good seal on cable entry points to the enclosure.
On my boards I used closed cell neoprene gaskets and have not had any issues with water ingress but I only occasionally ride through puddles and never intentionally ride when it is raining.
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The adhesive lined heat shrink is the bomb for water proofing.
I’ve made a few silicone/fabric bags that all the electrical components and batteries went in. It could be sealed then opened again for battery swapping. It was not esk8 related project. A bit of a pain in the ass to make but worked well in our tests.
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Lately I have moved on from “waterproof” and started doing “water resistant” only, mostly because it’s far more serviceable.
Also, once I discovered butyl tape, my water resist game went up tenfold… That stuff is the be-all and end-all of enclosure water resist game.
Also, having no holes other than a sealed (from the inside) charge port helps immensely. Epoxy all Amass XT- and MR- connectors male end through the enclosure, and no leaks.
Never run wires or cabling through the enclosure, and do not use cable glands or similar items. Don’t run wires over the edge of the enclosure either.
This is my newest “best way” to make stuff work in any environment, dust, water, brine, whatever.
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So im guessing you’re using a push to start to turn your board on?
It’s roll to start.
The opposite of pushing a button to start.
You knew what I meant…
On the contrary, my first instinct is always “pushing a button”
Why is this? to avoid having holes in the enclosure? wouldn’t the external wire be vulnerable
now #fuckpushing has a new meaning also 
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Harder to waterproof, connectors are “easy”. Also with cables, if you don’t make sure it’s water proof on the other end, for example, inside the motor, water will enter the enclosure from inside the wires over the months and years
Ok but then how are you supposed to connect the battery/esc to the motors? Transmit the energy wirelessly? 
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Epoxy the male end (with the pins, not the holes) of a connector through the enclosure.
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Why this?
Is this true for all wires?
Interested to learn otherwise, but I find it difficult to believe enough water will travel the 6" -12" from motor to VESC, between the copper strands and insulation, to cause problems inside the enclosure. Especially if your wiring orientation isn’t a downward angle from motor to enclosure (i.e. the common vertical wiring from motor). And if this is a real concern, a dab of silicone sealant / potting compound at the VESC end should close up a possible opening, assuming abrasion doesn’t cause a break somewhere else.
If we’re just talking inside a loose jacket, totally plausible.
Has anyone had this happen to them?
Edit:
May be worth considering wet rated wire, i.e. MTW wire
Don’t know if all but probably, its the capillary effect that makes the water go, each strand is round, so you have plenty of space for the water
If you just ride once in a while in the rain of some small puddle probably won’t happen, but if you are a madman (@b264) it can happen
In a board I never had this happen, but on more than one RC car
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Maybe obvious, but an important note nonetheless -
Unless your enclosure/deck geometry doesn’t allow for some reason (pre-drilled), your screws (and mounting holes) need to go OUTSIDE your enclosure gasket. Otherwise you’ve sealed your electronics up all tidy… and then drilled 10 nice new ingress points
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I’ve had that happen not just on esk8s but also the house I used to own, water entered the main breaker box in the basement, by coming in through the power wire, between the conductors and the insulation around the cable.
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I used corrosion x waterproof spray on my previous board. I highly recommend. Watch this:https://m.youtube.com/watch?v=s4z8QMgTEA4 I also put a decadent pack inside the enclosure and silicone caulking around it and the wire holes. I went through lots of water no problem.
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