There's truly no such thing as 'easier'- it's going to depend on one's experience and particular situation, and ultimately which system they prefer. For example, the iOS is a very user friendly system (on top of high quality hardware to boot), but sometimes getting things configured just right w/ Outlook isn't always the easiest task.
AFAIK, a lot of folks are using Samsung Kies (software) to perform the sync on Android devices. OTOH, I know a lot of folks who have had success using Companionlink (third party software) for iPhone. There are other methods too numerous to mention here.
If you use MS Exchange for email, it would be even easier yet. I recommend you consider a cloud based solution as well to potentially avoid having to constantly sync with a PC. Using Gmail & Google Calendar on an Android based device is a breeze IMO and E.
I am trying to decide between the two. I use Outlook for my email, contacts, calendar and sync between my computer and current phone(Blackberry) Which phone (Samsung or iphone) will be the easiest to transfer my data to and sync with my computer? What do I have to do to do that?