As mentioned, lifting weight off the shackles by lifting the frame usually does the trick. In many cases, even if the bolts are aligned correctly with the hole at 9 o'clock or 3 o'clock, it can be very difficult. I have found that, as the bushings wear, those holes can get filled with bronze (or plastic if the bushings are plastic) and will require removal of the bolt. That's a good time to inspect the bushings and bolts.
It might be safe to assume that more frequent greasing would reduce the likelihood the holes will get plugged.
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2020 Eagle HT 30.5 CKTS Modern Farmhouse (16" wheels, spring shackles set on lower hole of frame, SumoSprings TSS-107-40, standard kingpin, B&W Companion slider, TST-507 TPMS, Progressive Industries hardwired 50A EMS HW-50C)
2019 F250 SRW SuperCab 4X4 SB 6.2 (10,000# GVW) 3.73 Axle 18" wheels
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