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My contribution. I want a flatter countersink bit like this that is the angle of hardware so you can screw from the top without grip bunching up.
What you are looking for is a 90° countersink, which is a fairly common one. That's the angle of the bolts.
Or you take a"normal" metaldrill (118°), what I prefer.
What I do is (when I have the time and want a good outcome):
Put the trucks on before gripping, pull tight, take off, grip, pin the holes with a nail, give the drill a spin by hand to just remove the grip over the imprint of the hardware, set up.
As this has already gotten technical:
I wish there would be a tool to rethread truckbolts from the in to the outside.
Ugh, how can I describe it ?
Like a split threader you can put on the "healthy" part, instead of the normal ones, where you most likely fuck up the angle and/or make a second thread accidentally. Because naturally it doesn't work to repair the end when you need that end to set up the tool. If this makes any sense.
edited 'cause of bad quoting
This is the sort of thing that makes me smile.
I knew someone that would use a normal screw and power drill to screw through every bolt hole into a scrap piece of wood to get the simple imprinted head without cutting into the wood at all, then the deck bolts would fit in way more smoothly every time.
When setting up new boards, I usually just use a hand phillips screw driver on the deck bolt holes to get rid of excess grip and the Shortys bolts (smaller heads) never really have any issues going into the board, but if you are using larger head deck bolts, having the grip as well as the holes routed does help.
Been thinking about doing a "How to..." on this, so maybe this is the inspiration to get one done.
Good read!
Edit: As for the second part, re Ace nuts that are reathreaders, so when the nut has been on and the end of the axle is messed up, by undoing the nut will actually (in theory cause I haven't seen it work) re thread the axle thread as you take it off.
Might be worth looking into.
I always use more washers on the axles so the nuts sit flush, so there are no axle end issues, but some others I skate with have also had so many issues as they don't like washers that they grind off the excess axle end to the correct length for one washer on the inside and just the nut on the outside. It is pretty extreme, but they say it works.
Keeping a few sets of spare nuts is often handy too.