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TBH, it sounds like the threads on the bolt are fubar in a specific section. Most likely as you've been working it back and forth it has torn threads out, as you loosen the bolt, this section enters the nut, now you're spinning a round shaft inside the nut, there's no threads here. Use something similar to a claw on a hammer that will fit either side of the bolt head and try to apply downward force while also undoing it. The idea is to attempt to catch a thread, or just rip the f**ker out. Caution on ripping out, as it could bend/maime/mangle what the captive nut attaches to. If the captive nut is actually okay, you could do the dirty part of cutting the head off the bolt, then cut a slit in the end of the thread that's now exposed and then screw it up and into the area the captive nut is until it falls out the other side. However, this does risk the remainder of the bolt rusting over time and damaging near the captive nut and also making it rust. However, so can cutting pieces of panel work out to access this area if you don't reseal it properly.
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