Did you snap your w2 nozzles while trying to remove the shure olives? On my W4's, I had an issue with one pair getting stuck, which i ended up using a knife to carefully cut them off. From then on, I just didn't push the olives all the way to the bottom of the tube. There's still 1-2mm between the IEM and the olives so you can see the stalk a little bit. They've never fallen off, and I've taken them off and put them back on several times with no issues.
When you first get Shure SE535's, I had a bit of trouble removing the tips, and I recall reading that some people said to put the IEM's in the freezer and it'll make it easier to remove the tips. I was uncomfortable doing this myself, so I didn't, but it might be worth looking into.... although I feel my method works the best. I get a deeper insertion with my way, which I like.