Tell me your swaddle dropping success stories and horror stories

My son is 5 months and still fully swaddled. He has rolled a few times but not enough to be a problem for swaddling...yet. He is now too big for the Merlin suit I was given. He doesn’t like the Love to Dream arms up swaddle (he prefers his arms out in a T). If I leave one out of a regular swaddle or a Halo sleep sack swaddle, he cries until I wrap it back up. I’ve never done this before. Do I just go cold turkey and endure a couple weeks of sleep hell?