I am going to go out on a limb and say it does matter and I'll tell why why I think it does:
Cello on protects you cigars from damaging the wrapper during handling/storage. Also, during long term aging, there are many people who have stated that cigars aged in their cello had more flavor whaen smoked. Now this was for cigars from the same box, some had the cello taken off. If you dont have a large fridgedor or several coolerdor's, that chance that anything get's aged past 3-4 years is slim. But if you do have something set up for long term storage, why take a chance, keep the cellos on.
Now cello off is something I know a little more about. I have bought a ton of cigars from JR's. I really love their customer service and price point. But with that, you know to expect cigars that are shipped wet. If I don't plan on letting them age, I take the cello off immediately. They tend to climatize much faster to the humidor, beoming smokable sooner. Also, sick cigars will get better faster with cello off. Habano's are not the only cigar's that have sick periods.
So there you have it. I say look at your situation and see how either situation will apply to you. Hope that helps some.
Emo