Anyone have experience with a deck being remounted a bunch of times and the bolts really needing to be sunken in there for the proper tightness? I hate seeing it so I've been gripping over the bolts to kinda pull an out of sight out of mind. Also noticed last regrip the top ply has some pressure cracks around the bolt holes probably from so many remounts and countersinking too deep. I only really have madness about this cause I don't want to risk ovalizing the baseplate holes since they're converted/inverted baseplates and must be protected/reused forever if I can manage it. I do use those Ace shock pads which I feel helps lessen the chance of loosening.
Often my usual bolts like Shortys or similar with small heads are great for new boards, but then after a few changes, other bolt brands with bigger heads fit better, or in boards from other people that have been sunk in too far or whatever people do with them.
Usually I wouldn't use the bigger head bolts at all, but I found they work well in those boards that smaller heads have pulled through a bit too far, so they make them look and seem a lot better in that regard, so I keep a number of each on hand in the shop area to use as needed.
Almost all boards will usually end up with stress cracks down the length of the board, so that in itself is not a big deal. Just watch for any that run across or diagonally from the bolts area, as usually they are the ones that are the start of the board breaking or weakening.
As long as the bolts are nice and snug, more so the nuts still retain the nyloc material to keep them tight, there should not need to be an overtightening of the deck bolts, but various things like shock pads, or cut up bike tube or even grip tape stuck to the baseplate will help to stop the trucks moving against the board.
I just put stickers on the board under the trucks, as I have a whole lot of old shop stickers I have cut up to sit nicely under each truck, stuck on to the deck before I set the board up, which I find is just enough to prevent the metal truck on wood issues that some people have, so I don't need a riser or anything else with standard Indy 55 mm height, but I find Thunder or other lower trucks can often do with a 1 or 2 mm thin riser to just give them a touch more clearance with regular sized wheels, which in turn can help to prevent any truck movement on the board too.
Edit:
Going back to the nuts thing, the test I use with any is if I can tighten the nut completely on by hand, then the nyloc is done and it goes in the bin or will not be used again. Anything that still keeps the nyloc from letting the nut loosen itself off is good to use again and shouldn't have any problems there.
You can buy replacement nuts from hardware suppliers too, boxes of 100 or more are fairly cheap and keep bolts going for a lot longer than people might use them, or are good to have as spares just in case anyone loses some too.