any tips or suggestions are always welcomed.
Sometimes a bezel removal will bring the crystal retaining ring along with it. Even if it doesn't, it can be reassembled that way as shown in the pic below. This is actually the Rolex official right way to remove and reinstall these pieces. But they also use and sell an expensive tool that uses vacuum suction for removal and the right pressure in the right places on replacement. It's possible to reinstall the bezel with hytrel ring and retaining ring in place onto a rep, but I would remove the insert first.
To attempt this, any die that fits into the empty bezel well would work, the bezel will push the retaining ring down. I like to press the retaining ring separately so I can see how it seats and make sure it is down evenly all the way around.
There are differences among reps in how tightly a retaining ring, crystal gasket, and crystal fit on a case so doing this may be easy or may be more difficult but it shouldn't damage any parts as long as the insert is out and the hytrel ring is properly seated below the crystal retaining ring lip.
If you want to try to find something to press the retaining ring first onto the case, take the ring with you to a hardware or big box store and look for a thick washer or piece of PVC pipe with the right inside diameter to catch the ring but miss the crystal. You can press the ring with a small flat board on top of the washer and the case flat on a bench. Or protect the case and use a vise.