It looks as though you may be a little thin already in the working section. What poundage is it pulling right there? Also, are you pulling 20-30 pulls to work the wood after each scraping?
Remember that wood doesn't want to bend, so when you're tillering you aren't just taking off wood to get it to bend without breaking. Every time you scrape you expose a brand new surface and you have to "teach" that new wood how to bend. If you don't teach it properly, or in other words if you don't work the wood between scraping, you will wind up going way too thin.
Also, the 550 will stretch, but only so much. If you're working the wood correctly then you will negate the stretching of the paracord after the first 4 to 5 scrapings.