Are there any risks with converting an ESP to an ESM file? I could be wrong but I seem to recall bhl saying that there were dialogue issues he had to fix when he converted Rise of House Telvanni to ESM format.
I didn't have any dialogue issues to fix because of the esp to esm conversion (done with Wrye Mash by the way.) The only tricky thing with esm-files is that they are loaded first, and every esp-file can override their dialogue. So I had to apply elaborate filters to make sure that RoHT should work even under unfavorable conditions (alongside esp-files that use the same topics, for example). When working with an esp-file, a modder can resort to setting it to a later date than most other plugins. With esm-files, that isn't an option.
Enchanted editor breaks files often? Is this something that I would notice right away or will the mod load and I just won't know it is broken until halfway into a game?
Even though the Enchanted Editor officially still is in Beta, it is very reliable. I have only found it to produce errors when I altered some dialogue with it. After changing that dialogue, the whole dialogue entry's structure looked strange, like a mixture of dialogue and script. :shrug: For cleaning mods, checking their structure, changing their masters, and many other purposes, it is one of the best tools available.