If it's on Rogers, it is $25 for a SIM card, which can be purchased from a number of places, and you must purchase at least a $20 card for it for the initial activation. There is no activation charge, and the entire procedure can be done, either by yourself online or over the telephone, or in a Rogers certified store (which usually will charge between $20-50 for the work). If you sign up online (the easiest way) all it needs is your personal info, as well as the SIM card number, and the phone's IMEI - a long number, but clearly labeled and is located on the inside of the V360 behind the battery. As well, you'll need the pay-as-you-go input number you get when you purchase the $20 time, usually found on the receipt to activate it. Should you do manual top-ups, it can be done for free over the phone by dialing *611 from your cell, though it is annoying with the automated system.
The option will be there to get monthly top-ups charged onto a credit card (or to manually get cards yourself), as well as whether you want extras like voicemail (which is included, and just uses your airtime) and which specific plans you want to use. When choosing the plans, make sure you check out the Rogers pay-as-you-go subsite to get the specifics on each one to find one that fits. Once done, it takes about 2-4 hours for them to get your phone number set up and working, but that's enough time for you to get 'er charged up and ready to use. And that's it.
The good thing about the online signup is that it gives you a printable sheet with all your vitals on it, like your phone number and your plan details, which normally you'd have to write down were you to do it over the phone.
To answer the other part of your question: a V360 charger costs about $30 for a car charger, and $35 for a home charger. I know for a fact that The Source by Circuit City sells the Motorola ones, as does the Rogers outlets and most Future Shops. There are cheaper ones available at places like Wal-mart, but their quality is pretty bad. There's only about 3 ends for Motorola phones, so it isn't hard to find the right one; just fit the end. I know when I ran a Source store, we just popped one out of the case to make absolutely sure it fit in your phone. Not to sound like a shill, but you can buy everything: the charger, the SIM card and the time, right there in one shot, and for the extra fee (which they'll almost always waive if you're nice and don't waste their time) they'll activate it for you right there, which is nice because their activation program will give you a working phone number right away, instead of having to wait for a few hours for your phone to get up and running.