Do you roll for control anytime you enter the cloak even if it's only an RP thread or non-stat training? It's a skill, yes, but the effect is one that can be used in RP obviously. I know that skills, such as the water/tree walking amongst others, can be used in an RP thread/RP Training without it becoming a stat/skill battle or thread (Whatever you'd prefer to call it) but the nature of the 'beast' as it were with Yokai are something altogether different.
I've Copy/Pasted the in formation regarding the "Cloak of the Nekomata" (My Yokai) And the Cloak Rules/First rank of it from my page to make things a bit easier for you. I bolded the portion regarding regarding the roll. I'm guessing by the 'upkeep'/'setup phase' mentioning, it might only activate if the thread's already a stat one. Could be wrong though, would be helpful to know.
Next question. Regarding this. Is it highest level they've purchased, or highest level they Could purchase? Say, I only have Rank 1, but I'm level 40 (Thus could purchase rank 2) and I haven't bought that rank yet.. do I go into Rank 1 or Rank 2 in this state?