Could you not retap the stripped hole?
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I’ve had luck using the SS m4x8mm uxcell inserts off amazon. Hole size is of paramount importance as others have stated. Feel like I’ve got it down now. Drop of gorilla glue in the hole, insert and thread a bolt in and out while wiping off with a rag a few times before glue completely cures to keep threads clear.
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Do you guys use locktite between the screw and the insert?
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Recommended if you offroad. I’ve lost one screw after a off-road session. 
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I use half the amount I normally would of blue
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I’ve read that some people use a rubber o-ring too? Anyone care to chime in on that?
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Timo does that in his bergmeister wheel rims (not talking about the valve stem). Vibrations only hurt so I say do it.
they are indeed extremely difficult to remove but if you rest a soldering iron tip inside the thread area of the insert it will degrade the epoxy enough to start twisting it back out.
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not the heavy stuff, the lighter stuff like the blue 242. You’ll twist out your inserts if you use something too heavy.
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Hell, I don’t even use loctite on inserts for this reason honestly. I use some some of those nylon washers underneath the sexy little fender washers. They help to give tension.
Sure, you need to tighten them every once and a while, but you definitely won’t pull out your inserts. Been there, done that.
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squishing some wet silicone into the threads when putting the screws in works well too. Keeps them from falling out and doesn’t give your hex key any grief.
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This is also an excellent choice for threadlocking around polycarbonate - I learned the hard way that regular threadlocking compounds cause cracking/crazing.
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Does anyone use the hammer in inserts?
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Yes, they are especially useful if you want to completely destroy a deck because it has a vendetta against your family. Make the SoB bleed!!! 
For real though, they arent great. If you get the hole so the inserts are tight the deck will crack, if you get it too loose they will just fall out. Maybe if you used epoxy, but still there’s nothing surface to surface that grabs.
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For a bamboo/maple penny board I was thinking of putting countersink heads from the top and locking then from the bottom with loctite and a hammer insert so I can cover the top with grip tape and then have easy time to remove the enclosure.
Suggested alternative? Can I put JB weld in the hole to lock the screw in? (I can get it in without getting the threads fucked). BTW it’s an M5
use cinch/rivet nuts with ribbed walls, they will probably work well.
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That’s enough torque to hold the screw?
theres a lip at the top, put epoxy in the drilled hole and on the side of the cinch nut. should be good.
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These are also an option
Using these on a thin flexy deck. Have taken the enclosure on/off about 10 times and so far so good. no epoxy or anything.
Ribbed for the boards pleasure 
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